JPH0456016B2 - - Google Patents

Info

Publication number: JPH0456016B2
Authority: JP; Japan
Prior art keywords: optically active; reaction; ethylmagnesium; solution; alkanols
Prior art date: 1988-04-28
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

Application number

JP10389888A

Other languages

English (en)

Japanese (ja)

Other versions

JPH01275541A (ja

Inventor

Junko Umezawa

Osamu Takahashi

Keizo Furuhashi

Original Assignee

Nippon Mining Co

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.)

1988-04-28

Filing date

1988-04-28

Publication date

1992-09-07

1988-04-28 Application filed by Nippon Mining Co filed Critical Nippon Mining Co

1988-04-28 Priority to JP10389888A priority Critical patent/JPH01275541A/ja

1989-11-06 Publication of JPH01275541A publication Critical patent/JPH01275541A/ja

1992-09-07 Publication of JPH0456016B2 publication Critical patent/JPH0456016B2/ja

Status Granted legal-status Critical Current

Links

-1 ethylmagnesium halide Chemical class 0.000 claims description 12
150000001879 copper Chemical class 0.000 claims description 7
238000004519 manufacturing process Methods 0.000 claims description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 23
239000000243 solution Substances 0.000 description 10
238000000034 method Methods 0.000 description 7
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
239000003960 organic solvent Substances 0.000 description 6
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
NJWSNNWLBMSXQR-MRVPVSSYSA-N (2r)-2-hexyloxirane Chemical compound CCCCCC[C@@H]1CO1 NJWSNNWLBMSXQR-MRVPVSSYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
239000004593 Epoxy Substances 0.000 description 3
150000001335 aliphatic alkanes Chemical class 0.000 description 3
230000000694 effects Effects 0.000 description 3
FRIJBUGBVQZNTB-UHFFFAOYSA-M magnesium;ethane;bromide Chemical compound [Mg+2].[Br-].[CH2-]C FRIJBUGBVQZNTB-UHFFFAOYSA-M 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
150000002924 oxiranes Chemical group 0.000 description 3
DTDMYWXTWWFLGJ-JTQLQIEISA-N 4-Decanol Natural products CCCCCC[C@@H](O)CCC DTDMYWXTWWFLGJ-JTQLQIEISA-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
DTDMYWXTWWFLGJ-UHFFFAOYSA-N decan-4-ol Chemical compound CCCCCCC(O)CCC DTDMYWXTWWFLGJ-UHFFFAOYSA-N 0.000 description 2
238000004821 distillation Methods 0.000 description 2
HOWGUJZVBDQJKV-UHFFFAOYSA-N docosane Chemical compound CCCCCCCCCCCCCCCCCCCCCC HOWGUJZVBDQJKV-UHFFFAOYSA-N 0.000 description 2
SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
BLHLJVCOVBYQQS-UHFFFAOYSA-N ethyllithium Chemical compound [Li]CC BLHLJVCOVBYQQS-UHFFFAOYSA-N 0.000 description 2
239000000203 mixture Substances 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
RBACIKXCRWGCBB-UHFFFAOYSA-N 1,2-Epoxybutane Chemical compound CCC1CO1 RBACIKXCRWGCBB-UHFFFAOYSA-N 0.000 description 1
DSZTYVZOIUIIGA-UHFFFAOYSA-N 1,2-Epoxyhexadecane Chemical compound CCCCCCCCCCCCCCC1CO1 DSZTYVZOIUIIGA-UHFFFAOYSA-N 0.000 description 1
FRCQVIXJQKSHHF-UHFFFAOYSA-N 1-(morpholin-4-ylmethyl)cyclohexan-1-amine Chemical compound C1COCCN1CC1(N)CCCCC1 FRCQVIXJQKSHHF-UHFFFAOYSA-N 0.000 description 1
WHNBDXQTMPYBAT-UHFFFAOYSA-N 2-butyloxirane Chemical compound CCCCC1CO1 WHNBDXQTMPYBAT-UHFFFAOYSA-N 0.000 description 1
MPGABYXKKCLIRW-UHFFFAOYSA-N 2-decyloxirane Chemical compound CCCCCCCCCCC1CO1 MPGABYXKKCLIRW-UHFFFAOYSA-N 0.000 description 1
IOHJQSFEAYDZGF-UHFFFAOYSA-N 2-dodecyloxirane Chemical compound CCCCCCCCCCCCC1CO1 IOHJQSFEAYDZGF-UHFFFAOYSA-N 0.000 description 1
CEUXMUYHMURJFZ-UHFFFAOYSA-N 2-heptadecyloxirane Chemical compound CCCCCCCCCCCCCCCCCC1CO1 CEUXMUYHMURJFZ-UHFFFAOYSA-N 0.000 description 1
GXOYTMXAKFMIRK-UHFFFAOYSA-N 2-heptyloxirane Chemical compound CCCCCCCC1CO1 GXOYTMXAKFMIRK-UHFFFAOYSA-N 0.000 description 1
QBJWYMFTMJFGOL-UHFFFAOYSA-N 2-hexadecyloxirane Chemical compound CCCCCCCCCCCCCCCCC1CO1 QBJWYMFTMJFGOL-UHFFFAOYSA-N 0.000 description 1
NJWSNNWLBMSXQR-UHFFFAOYSA-N 2-hexyloxirane Chemical compound CCCCCCC1CO1 NJWSNNWLBMSXQR-UHFFFAOYSA-N 0.000 description 1
WUFZMCBAEIQTDA-UHFFFAOYSA-N 2-nonadecyloxirane Chemical compound CCCCCCCCCCCCCCCCCCCC1CO1 WUFZMCBAEIQTDA-UHFFFAOYSA-N 0.000 description 1
LXVAZSIZYQIZCR-UHFFFAOYSA-N 2-nonyloxirane Chemical compound CCCCCCCCCC1CO1 LXVAZSIZYQIZCR-UHFFFAOYSA-N 0.000 description 1
BHZBVWCLMYQFQX-UHFFFAOYSA-N 2-octadecyloxirane Chemical compound CCCCCCCCCCCCCCCCCCC1CO1 BHZBVWCLMYQFQX-UHFFFAOYSA-N 0.000 description 1
AAMHBRRZYSORSH-UHFFFAOYSA-N 2-octyloxirane Chemical compound CCCCCCCCC1CO1 AAMHBRRZYSORSH-UHFFFAOYSA-N 0.000 description 1
XSNXNMMWBCZUSS-UHFFFAOYSA-N 2-pentadecyloxirane Chemical compound CCCCCCCCCCCCCCCC1CO1 XSNXNMMWBCZUSS-UHFFFAOYSA-N 0.000 description 1
NMOFYYYCFRVWBK-UHFFFAOYSA-N 2-pentyloxirane Chemical compound CCCCCC1CO1 NMOFYYYCFRVWBK-UHFFFAOYSA-N 0.000 description 1
SYURNNNQIFDVCA-UHFFFAOYSA-N 2-propyloxirane Chemical compound CCCC1CO1 SYURNNNQIFDVCA-UHFFFAOYSA-N 0.000 description 1
QMIBIXKZPBEGTE-UHFFFAOYSA-N 2-tridecyloxirane Chemical compound CCCCCCCCCCCCCC1CO1 QMIBIXKZPBEGTE-UHFFFAOYSA-N 0.000 description 1
ZKAPVLMBPUYKKP-UHFFFAOYSA-N 2-undecyloxirane Chemical compound CCCCCCCCCCCC1CO1 ZKAPVLMBPUYKKP-UHFFFAOYSA-N 0.000 description 1
229910021595 Copper(I) iodide Inorganic materials 0.000 description 1
CDKFWIMBZAUBRS-UHFFFAOYSA-M [I-].CC[Mg+] Chemical compound [I-].CC[Mg+] CDKFWIMBZAUBRS-UHFFFAOYSA-M 0.000 description 1
239000003905 agrochemical Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
ODWXUNBKCRECNW-UHFFFAOYSA-M bromocopper(1+) Chemical compound Br[Cu+] ODWXUNBKCRECNW-UHFFFAOYSA-M 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
239000010949 copper Substances 0.000 description 1
ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 1
DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 1
LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 1
GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000005262 ferroelectric liquid crystals (FLCs) Substances 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
YCCXQARVHOPWFJ-UHFFFAOYSA-M magnesium;ethane;chloride Chemical compound [Mg+2].[Cl-].[CH2-]C YCCXQARVHOPWFJ-UHFFFAOYSA-M 0.000 description 1
244000005700 microbiome Species 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
238000005191 phase separation Methods 0.000 description 1
230000006340 racemization Effects 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000010992 reflux Methods 0.000 description 1
238000010898 silica gel chromatography Methods 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
230000002194 synthesizing effect Effects 0.000 description 1
239000004711 α-olefin Substances 0.000 description 1

Landscapes

Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

JP10389888A 1988-04-28 1988-04-28 光学活性を有する４−アルカノール類の製造方法 Granted JPH01275541A (ja)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP10389888A JPH01275541A (ja)	1988-04-28	1988-04-28	光学活性を有する４−アルカノール類の製造方法

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP10389888A JPH01275541A (ja)	1988-04-28	1988-04-28	光学活性を有する４−アルカノール類の製造方法

Publications (2)

Publication Number	Publication Date
JPH01275541A JPH01275541A (ja)	1989-11-06
JPH0456016B2 true JPH0456016B2 (2)	1992-09-07

Family

ID=14366241

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP10389888A Granted JPH01275541A (ja)	1988-04-28	1988-04-28	光学活性を有する４−アルカノール類の製造方法

Country Status (1)

Country	Link
JP (1)	JPH01275541A (2)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US7589221B2 (en)	2003-06-10	2009-09-15	Ono Pharmaceutical Co., Ltd.	Process for producing (2R)-2-propyloctanoic acid and intermediate therefor

1988
- 1988-04-28 JP JP10389888A patent/JPH01275541A/ja active Granted

Also Published As

Publication number	Publication date
JPH01275541A (ja)	1989-11-06

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