CH628631A5 - Process for the preparation of butenolide derivatives - Google Patents

Process for the preparation of butenolide derivatives Download PDF

Info

Publication number: CH628631A5
Authority: CH; Switzerland
Prior art keywords: formula; compound; single bond; methyl; bond
Prior art date: 1976-09-13

Application number

CH1115677A

Other languages

German (de)

English (en)

Inventor

Alan Woodworth Johnson

Ahmed Hassanali-Walji

Original Assignee

Int Dev Res Center

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.)

1976-09-13

Filing date

1977-09-13

Publication date

1982-03-15

1977-09-13 Application filed by Int Dev Res Center filed Critical Int Dev Res Center

1982-03-15 Publication of CH628631A5 publication Critical patent/CH628631A5/de

Links

238000000034 method Methods 0.000 title claims description 28
238000002360 preparation method Methods 0.000 title claims description 7
SQEBMLCQNJOCBG-HVHJFMEUSA-N (5s)-3-(hydroxymethyl)-5-methoxy-4-methyl-5-[(e)-2-phenylethenyl]furan-2-one Chemical class C=1C=CC=CC=1/C=C/[C@]1(OC)OC(=O)C(CO)=C1C SQEBMLCQNJOCBG-HVHJFMEUSA-N 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims description 26
159000000000 sodium salts Chemical class 0.000 claims description 20
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
239000001257 hydrogen Substances 0.000 claims description 7
229910052739 hydrogen Inorganic materials 0.000 claims description 7
239000000376 reactant Substances 0.000 claims description 6
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims description 5
125000004432 carbon atom Chemical group C* 0.000 claims description 5
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
OZJPLYNZGCXSJM-UHFFFAOYSA-N 5-valerolactone Chemical compound O=C1CCCCO1 OZJPLYNZGCXSJM-UHFFFAOYSA-N 0.000 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
229910001413 alkali metal ion Inorganic materials 0.000 claims description 3
125000001309 chloro group Chemical class Cl* 0.000 claims description 3
239000003085 diluting agent Substances 0.000 claims description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
239000003960 organic solvent Substances 0.000 claims description 2
125000004430 oxygen atom Chemical group O* 0.000 claims description 2
239000002904 solvent Substances 0.000 claims description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
GCVGDGFZLSSUIO-UHFFFAOYSA-N 4-chloro-2h-furan-5-one Chemical compound ClC1=CCOC1=O GCVGDGFZLSSUIO-UHFFFAOYSA-N 0.000 description 5
239000000203 mixture Substances 0.000 description 5
239000011734 sodium Substances 0.000 description 4
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical class CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 3
-1 alkali metal salt Chemical class 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
RZQNZDURDLIZRR-UHFFFAOYSA-N 4-chloro-3-methyl-2h-furan-5-one Chemical compound CC1=C(Cl)C(=O)OC1 RZQNZDURDLIZRR-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
YNBMDVQFFDOHBI-UHFFFAOYSA-N C(=O)CC(=O)O.OC1CC2C(C1)O2 Chemical compound C(=O)CC(=O)O.OC1CC2C(C1)O2 YNBMDVQFFDOHBI-UHFFFAOYSA-N 0.000 description 1
241000263342 Orobanche crenata Species 0.000 description 1
241000404576 Phelipanche aegyptiaca Species 0.000 description 1
241000201310 Phelipanche ramosa Species 0.000 description 1
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
241000208000 Striga Species 0.000 description 1
240000001705 Striga asiatica Species 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
NPOMSUOUAZCMBL-UHFFFAOYSA-N dichloromethane;ethoxyethane Chemical compound ClCCl.CCOCC NPOMSUOUAZCMBL-UHFFFAOYSA-N 0.000 description 1
238000004821 distillation Methods 0.000 description 1
125000003700 epoxy group Chemical group 0.000 description 1
239000000284 extract Substances 0.000 description 1
230000002363 herbicidal effect Effects 0.000 description 1
239000005457 ice water Substances 0.000 description 1
230000003071 parasitic effect Effects 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000012258 stirred mixture Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/04—Ortho-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/58—One oxygen atom, e.g. butenolide
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/60—Two oxygen atoms, e.g. succinic anhydride

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Furan Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Plural Heterocyclic Compounds (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)

CH1115677A 1976-09-13 1977-09-13 Process for the preparation of butenolide derivatives CH628631A5 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB3776076		1976-09-13

Publications (1)

Publication Number	Publication Date
CH628631A5 true CH628631A5 (en)	1982-03-15

Family

ID=10398816

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH1115677A CH628631A5 (en)	1976-09-13	1977-09-13	Process for the preparation of butenolide derivatives

Country Status (9)

Country	Link
JP (1)	JPS5334769A (da)
BE (1)	BE858646A (da)
CA (1)	CA1104145A (da)
CH (1)	CH628631A5 (da)
DE (1)	DE2740801A1 (da)
DK (1)	DK406777A (da)
FR (1)	FR2364212A1 (da)
NL (1)	NL7709873A (da)
SE (1)	SE7710205L (da)

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1470097A (en) *	1974-04-18	1977-04-14	Int Dev Res Centre	Alpha-butyrolactone derivatives as germination factors

1977
- 1977-09-08 NL NL7709873A patent/NL7709873A/xx not_active Application Discontinuation
- 1977-09-09 DE DE19772740801 patent/DE2740801A1/de not_active Withdrawn
- 1977-09-09 FR FR7727398A patent/FR2364212A1/fr not_active Withdrawn
- 1977-09-09 CA CA286,399A patent/CA1104145A/en not_active Expired
- 1977-09-12 SE SE7710205A patent/SE7710205L/xx unknown
- 1977-09-13 DK DK406777A patent/DK406777A/da not_active Application Discontinuation
- 1977-09-13 JP JP10955677A patent/JPS5334769A/ja active Pending
- 1977-09-13 CH CH1115677A patent/CH628631A5/de not_active IP Right Cessation
- 1977-09-13 BE BE180863A patent/BE858646A/xx unknown

Also Published As

Publication number	Publication date
NL7709873A (nl)	1978-03-15
CA1104145A (en)	1981-06-30
JPS5334769A (en)	1978-03-31
DK406777A (da)	1978-03-14
DE2740801A1 (de)	1978-03-16
BE858646A (fr)	1978-03-13
FR2364212A1 (fr)	1978-04-07
SE7710205L (sv)	1978-03-14

Legal Events

Date	Code	Title	Description
1983-05-31	PL	Patent ceased
2024-10-31	PL	Patent ceased

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