JPH0456016B2 - - Google Patents
Info
- Publication number
- JPH0456016B2 JPH0456016B2 JP10389888A JP10389888A JPH0456016B2 JP H0456016 B2 JPH0456016 B2 JP H0456016B2 JP 10389888 A JP10389888 A JP 10389888A JP 10389888 A JP10389888 A JP 10389888A JP H0456016 B2 JPH0456016 B2 JP H0456016B2
- Authority
- JP
- Japan
- Prior art keywords
- optically active
- reaction
- ethylmagnesium
- solution
- alkanols
- Prior art date
- 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
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)
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 (US07223432-20070529-C00017.png) | 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 (US07223432-20070529-C00017.png) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4742868B2 (ja) * | 2003-06-10 | 2011-08-10 | 小野薬品工業株式会社 | （２ｒ）−２−プロピルオクタン酸の製造方法、その中間体 |
-
1988
- 1988-04-28 JP JP10389888A patent/JPH01275541A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPH01275541A (ja) | 1989-11-06 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP3003327B2 (ja) | 光学活性アミン類の製法 | |
| JPH059416B2 (US07223432-20070529-C00017.png) | ||
| JPH0456016B2 (US07223432-20070529-C00017.png) | ||
| US4408063A (en) | Preparation of epihalohydrin enantiomers | |
| JPH0446935B2 (US07223432-20070529-C00017.png) | ||
| JP2582288B2 (ja) | 光学活性な１―フルオロ―２―アルカノール類及びその製造方法 | |
| JPS58198476A (ja) | ポリグリシジル誘導体の製造方法 | |
| JPH05261295A (ja) | 不斉誘起触媒 | |
| Youn et al. | Highly diastereoselective additions of methoxyallene and acetylenes to chiral α-keto amidesElectronic supplementary information (ESI) available: synthesis and spectroscopic data for 4b, 5g, 6b and 7b. See http://www. rsc. org/suppdata/cc/b1/b100355k | |
| US4588824A (en) | Preparation of epihalohydrin enantiomers | |
| JP2012184229A (ja) | ランジオロールのエナンチオ選択的合成のためのプロセス | |
| JPS6342626B2 (US07223432-20070529-C00017.png) | ||
| US6207847B1 (en) | Manufacture of optically active halohydrin trialkylsilyl ethers | |
| JP2649572B2 (ja) | 光学活性な２―フルオロ―２―メチル―１―アルカノール類及びその製造方法 | |
| JP2582289B2 (ja) | 光学活性を有する２―フルオロ―１―アルカノール類の製造方法 | |
| JP2640688B2 (ja) | カルバメート誘導体類及びそれらの製造方法 | |
| KR0126769B1 (ko) | (아릴)-(디메틸)-(3-(4-플루오로-3-아릴옥시페닐)프로필)실란의 제조방법 | |
| JPS6348269B2 (US07223432-20070529-C00017.png) | ||
| JPH0696564B2 (ja) | α−（ω−ヒドロキシアルキル）フルフリルアルコ−ル及びその製造法 | |
| JPH08217775A (ja) | 新規クラウンチオエーテル及びその遷移金属錯体並びにこれを用いる光学活性アルコールの製造方法 | |
| JP2669885B2 (ja) | （ｚ）―２―（３’，３’―ジメチルシクロヘキシリデン）エタノールの製法 | |
| JPH01193262A (ja) | （ｓ）‐グリセロール−１，２‐アセトナイドの製法 | |
| JPH0341056A (ja) | β―ヒドロキシアミノ化合物の製造方法 | |
| JP2906187B2 (ja) | フルオロフェノール類の製造法 | |
| SU620489A1 (ru) | Способ получени -силилированных -хлорвинилалкиловых эфиров |
