CA1271967A - Methode de preparation de furanes - Google Patents

Methode de preparation de furanes

Info

Publication number: CA1271967A
Authority: CA; Canada
Prior art keywords: hydrogen; protective group; halogen; blocked; detachable protective
Prior art date: 1985-12-27
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired - Lifetime

Application number

CA602,408A

Other languages

English (en)

Inventor

Hans Theobald

Rainer Becker

Walter Himmele

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

BASF SE

Original Assignee

BASF SE

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1985-12-27

Filing date

1989-06-09

Publication date

1990-07-24

1985-12-27 Priority claimed from CA000498662A external-priority patent/CA1268465A/fr

1989-06-09 Application filed by BASF SE filed Critical BASF SE

1989-06-09 Priority to CA602,408A priority Critical patent/CA1271967A/fr

1990-07-24 Application granted granted Critical

1990-07-24 Publication of CA1271967A publication Critical patent/CA1271967A/fr

2007-07-24 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 13
150000002240 furans Chemical class 0.000 title claims abstract description 11
-1 nitro- Chemical class 0.000 claims abstract description 12
125000006239 protecting group Chemical group 0.000 claims abstract description 10
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 9
239000001257 hydrogen Substances 0.000 claims abstract description 9
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 6
238000005984 hydrogenation reaction Methods 0.000 claims abstract description 5
125000003545 alkoxy group Chemical group 0.000 claims abstract description 4
125000003118 aryl group Chemical group 0.000 claims abstract description 4
125000004438 haloalkoxy group Chemical group 0.000 claims abstract description 4
125000001188 haloalkyl group Chemical group 0.000 claims abstract description 4
125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 3
125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 3
125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 7
WEQPBCSPRXFQQS-UHFFFAOYSA-N 4,5-dihydro-1,2-oxazole Chemical compound C1CC=NO1 WEQPBCSPRXFQQS-UHFFFAOYSA-N 0.000 claims description 4
229910052736 halogen Inorganic materials 0.000 claims description 4
150000002367 halogens Chemical group 0.000 claims description 4
125000005843 halogen group Chemical group 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 3
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims description 2
230000020477 pH reduction Effects 0.000 claims 1
150000002547 isoxazolines Chemical class 0.000 abstract description 9
239000000126 substance Substances 0.000 abstract description 5
150000002431 hydrogen Chemical class 0.000 abstract description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
238000006243 chemical reaction Methods 0.000 description 6
238000003786 synthesis reaction Methods 0.000 description 6
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
238000005481 NMR spectroscopy Methods 0.000 description 5
235000013350 formula milk Nutrition 0.000 description 5
150000002825 nitriles Chemical class 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
239000000706 filtrate Substances 0.000 description 4
125000000623 heterocyclic group Chemical group 0.000 description 4
239000000203 mixture Substances 0.000 description 4
239000002904 solvent Substances 0.000 description 4
239000007858 starting material Substances 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 3
239000000543 intermediate Substances 0.000 description 3
125000001424 substituent group Chemical group 0.000 description 3
HXVNBWAKAOHACI-UHFFFAOYSA-N 2,4-dimethyl-3-pentanone Chemical compound CC(C)C(=O)C(C)C HXVNBWAKAOHACI-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
150000001336 alkenes Chemical class 0.000 description 2
125000003342 alkenyl group Chemical group 0.000 description 2
150000001491 aromatic compounds Chemical class 0.000 description 2
150000002241 furanones Chemical class 0.000 description 2
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 2
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 2
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
239000002243 precursor Substances 0.000 description 2
238000007363 ring formation reaction Methods 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
238000006467 substitution reaction Methods 0.000 description 2
AFEOKIGLYCQHAZ-UHFFFAOYSA-N (5-benzylfuran-3-yl)methanol Chemical compound OCC1=COC(CC=2C=CC=CC=2)=C1 AFEOKIGLYCQHAZ-UHFFFAOYSA-N 0.000 description 1
SEWWFHKIKWFJNV-GQCTYLIASA-N (E)-2-methylbutanal oxime Chemical compound CCC(C)\C=N\O SEWWFHKIKWFJNV-GQCTYLIASA-N 0.000 description 1
CXISHLWVCSLKOJ-CLFYSBASSA-N (Z)-phenylacetaldehyde oxime Chemical compound O\N=C/CC1=CC=CC=C1 CXISHLWVCSLKOJ-CLFYSBASSA-N 0.000 description 1
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
KYDWIPDFXMLCGM-UHFFFAOYSA-N 4-benzyl-5-methylfuran-3-ol Chemical compound C(C1=CC=CC=C1)C1=C(OC=C1O)C KYDWIPDFXMLCGM-UHFFFAOYSA-N 0.000 description 1
USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
239000005695 Ammonium acetate Substances 0.000 description 1
101150041968 CDC13 gene Proteins 0.000 description 1
BZKFMUIJRXWWQK-UHFFFAOYSA-N Cyclopentenone Chemical class O=C1CCC=C1 BZKFMUIJRXWWQK-UHFFFAOYSA-N 0.000 description 1
241000282326 Felis catus Species 0.000 description 1
239000007832 Na2SO4 Substances 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
239000007868 Raney catalyst Substances 0.000 description 1
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
229910000564 Raney nickel Inorganic materials 0.000 description 1
239000005708 Sodium hypochlorite Substances 0.000 description 1
229910010062 TiCl3 Inorganic materials 0.000 description 1
NYMIJZDIYZUPNM-UHFFFAOYSA-N [3-benzyl-5-(hydroxymethyl)-4h-1,2-oxazol-5-yl]methanol Chemical compound O1C(CO)(CO)CC(CC=2C=CC=CC=2)=N1 NYMIJZDIYZUPNM-UHFFFAOYSA-N 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
229960000583 acetic acid Drugs 0.000 description 1
BKVVMFUJRYQWSL-UHFFFAOYSA-N acetic acid;2-methylprop-1-ene Chemical compound CC(C)=C.CC(O)=O.CC(O)=O BKVVMFUJRYQWSL-UHFFFAOYSA-N 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
229940043376 ammonium acetate Drugs 0.000 description 1
235000019257 ammonium acetate Nutrition 0.000 description 1
AXLOCHLTNQDFFS-BESJYZOMSA-N azastene Chemical compound C([C@H]1[C@@H]2CC[C@@]([C@]2(CC[C@@H]1[C@@]1(C)C2)C)(O)C)C=C1C(C)(C)C1=C2C=NO1 AXLOCHLTNQDFFS-BESJYZOMSA-N 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
230000001588 bifunctional effect Effects 0.000 description 1
150000001768 cations Chemical class 0.000 description 1
GPUADMRJQVPIAS-QCVDVZFFSA-M cerivastatin sodium Chemical compound [Na+].COCC1=C(C(C)C)N=C(C(C)C)C(\C=C\[C@@H](O)C[C@@H](O)CC([O-])=O)=C1C1=CC=C(F)C=C1 GPUADMRJQVPIAS-QCVDVZFFSA-M 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
239000013078 crystal Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
125000005594 diketone group Chemical group 0.000 description 1
238000004821 distillation Methods 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
STJIISDMSMJQQK-UHFFFAOYSA-N furan-3-ylmethanol Chemical compound OCC=1C=COC=1 STJIISDMSMJQQK-UHFFFAOYSA-N 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
230000006698 induction Effects 0.000 description 1
239000002917 insecticide Substances 0.000 description 1
238000002955 isolation Methods 0.000 description 1
150000002545 isoxazoles Chemical class 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000007788 liquid Substances 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
150000002923 oximes Chemical class 0.000 description 1
MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 description 1
125000004430 oxygen atom Chemical group O* 0.000 description 1
HVAMZGADVCBITI-UHFFFAOYSA-M pent-4-enoate Chemical compound [O-]C(=O)CCC=C HVAMZGADVCBITI-UHFFFAOYSA-M 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
229910003446 platinum oxide Inorganic materials 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
239000011814 protection agent Substances 0.000 description 1
150000003217 pyrazoles Chemical class 0.000 description 1
150000003222 pyridines Chemical class 0.000 description 1
150000008318 pyrimidones Chemical class 0.000 description 1
150000003233 pyrroles Chemical class 0.000 description 1
239000000376 reactant Substances 0.000 description 1
230000008707 rearrangement Effects 0.000 description 1
230000007017 scission Effects 0.000 description 1
SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
238000003756 stirring Methods 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
YONPGGFAJWQGJC-UHFFFAOYSA-K titanium(iii) chloride Chemical compound Cl[Ti](Cl)Cl YONPGGFAJWQGJC-UHFFFAOYSA-K 0.000 description 1
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
239000008096 xylene Substances 0.000 description 1
NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 1

Classifications

- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

CA602,408A 1985-12-27 1989-06-09 Methode de preparation de furanes Expired - Lifetime CA1271967A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA602,408A CA1271967A (fr)	1985-12-27	1989-06-09	Methode de preparation de furanes

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
CA000498662A CA1268465A (fr)	1984-12-29	1985-12-27	Isoxazolines utiles pour la preparation des furannes
CA602,408A CA1271967A (fr)	1985-12-27	1989-06-09	Methode de preparation de furanes

Related Parent Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000498662A Division CA1268465A (fr)	1984-12-29	1985-12-27	Isoxazolines utiles pour la preparation des furannes

Publications (1)

Publication Number	Publication Date
CA1271967A true CA1271967A (fr)	1990-07-24

Family

ID=33515043

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA602,408A Expired - Lifetime CA1271967A (fr)	1985-12-27	1989-06-09	Methode de preparation de furanes

Country Status (1)

Country	Link
CA (1)	CA1271967A (fr)

1989
- 1989-06-09 CA CA602,408A patent/CA1271967A/fr not_active Expired - Lifetime

Legal Events

Date	Code	Title	Description
2006-07-24	MKLA	Lapsed

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US4954633A (en)	1990-09-04	Isoxazolines as intermediates to furans
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US4025537A (en)	1977-05-24	Preparation of 3-carboalkoxy or 3-alkanoyl furans
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GB1594450A (en)	1981-07-30	1,3-oxathiolane sulphoxides and their use in the preparation of 5,6-dihydro-2-methyl-1,4-oxathiin derivatives
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US4044026A (en)	1977-08-23	Substituted succinaldehyde monoacetals
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SU677659A3 (ru)	1979-07-30	Способ получени 2,4-диметил-3карбоксанилидфурана
Patwardhan et al.	1976	Some 4-oxa-farnesane insect juvenile hormone mimics