JPS6357412B2 - - Google Patents
Info
- Publication number
- JPS6357412B2 JPS6357412B2 JP3878583A JP3878583A JPS6357412B2 JP S6357412 B2 JPS6357412 B2 JP S6357412B2 JP 3878583 A JP3878583 A JP 3878583A JP 3878583 A JP3878583 A JP 3878583A JP S6357412 B2 JPS6357412 B2 JP S6357412B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- general formula
- mmol
- fluoroalkyl
- reaction
- 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
- 125000001931 aliphatic group Chemical group 0.000 claims description 7
- 150000004808 allyl alcohols Chemical class 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 7
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- 125000004991 fluoroalkenyl group Chemical group 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 150000004820 halides Chemical class 0.000 claims description 2
- -1 isobutylmagnesium halide Chemical class 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 239000000047 product Substances 0.000 description 8
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 6
- 229910052731 fluorine Inorganic materials 0.000 description 6
- 239000011737 fluorine Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- PISHZENUSKYJSY-UHFFFAOYSA-N 1,1,1-trifluoro-4-phenylbut-3-yn-2-ol Chemical compound FC(F)(F)C(O)C#CC1=CC=CC=C1 PISHZENUSKYJSY-UHFFFAOYSA-N 0.000 description 3
- JVTSHOJDBRTPHD-UHFFFAOYSA-N 2,2,2-trifluoroacetaldehyde Chemical compound FC(F)(F)C=O JVTSHOJDBRTPHD-UHFFFAOYSA-N 0.000 description 3
- 150000001345 alkine derivatives Chemical class 0.000 description 3
- 238000000921 elemental analysis Methods 0.000 description 3
- 150000002367 halogens Chemical group 0.000 description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
- YSMZEMQBSONIMJ-UHFFFAOYSA-M magnesium;2-methanidylpropane;chloride Chemical compound [Mg+2].[Cl-].CC(C)[CH2-] YSMZEMQBSONIMJ-UHFFFAOYSA-M 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000002604 ultrasonography Methods 0.000 description 3
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 2
- UEXCJVNBTNXOEH-UHFFFAOYSA-N Ethynylbenzene Chemical group C#CC1=CC=CC=C1 UEXCJVNBTNXOEH-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 230000005587 bubbling Effects 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000010936 titanium Substances 0.000 description 2
- 229910052719 titanium Inorganic materials 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- AXKNZQYVSJHTGO-UHFFFAOYSA-N 1,1,1-trifluoropent-4-yn-2-ol Chemical compound FC(F)(F)C(O)CC#C AXKNZQYVSJHTGO-UHFFFAOYSA-N 0.000 description 1
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 1
- 101150065749 Churc1 gene Proteins 0.000 description 1
- 102100038239 Protein Churchill Human genes 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- YORCIIVHUBAYBQ-UHFFFAOYSA-N propargyl bromide Chemical compound BrCC#C YORCIIVHUBAYBQ-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 230000017105 transposition Effects 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3878583A JPS59164742A (ja) | 1983-03-09 | 1983-03-09 | α−（フルオロアルキル又はアルケニル）アリルアルコ−ル類の製造方法 |
| US06/586,943 US4532020A (en) | 1983-03-09 | 1984-03-07 | Process for preparing a β-(fluoroalkyl or fluoroalkenyl)-β-hydroxyalkyne |
| DE8484102515T DE3460013D1 (en) | 1983-03-09 | 1984-03-08 | Process for preparing a beta-(fluoroalkyl or fluoroalkenyl)-beta-hydroxyalkyne and an alpha-(fluoroalkyl or fluoroalkenyl)-allyl alcohol thereof |
| EP84102515A EP0118890B1 (en) | 1983-03-09 | 1984-03-08 | Process for preparing a beta-(fluoroalkyl or fluoroalkenyl)-beta-hydroxyalkyne and an alpha-(fluoroalkyl or fluoroalkenyl)-allyl alcohol thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3878583A JPS59164742A (ja) | 1983-03-09 | 1983-03-09 | α−（フルオロアルキル又はアルケニル）アリルアルコ−ル類の製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS59164742A JPS59164742A (ja) | 1984-09-17 |
| JPS6357412B2 true JPS6357412B2 (enrdf_load_stackoverflow) | 1988-11-11 |
Family
ID=12534949
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3878583A Granted JPS59164742A (ja) | 1983-03-09 | 1983-03-09 | α−（フルオロアルキル又はアルケニル）アリルアルコ−ル類の製造方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS59164742A (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH02114811U (enrdf_load_stackoverflow) * | 1989-02-25 | 1990-09-13 |
-
1983
- 1983-03-09 JP JP3878583A patent/JPS59164742A/ja active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH02114811U (enrdf_load_stackoverflow) * | 1989-02-25 | 1990-09-13 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS59164742A (ja) | 1984-09-17 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Linderman et al. | Oxidation of fluoroalkyl-substituted carbinols by the Dess-Martin reagent | |
| Zweifel et al. | Allenic zinc reagents. A remarkably regio-and diastereoselective synthesis of 2-substituted homopropargylic alcohols | |
| Kitazume et al. | Ultrasound-promoted hydroperfluoroalkylation of alkynes with perfluoroalkylzinc iodide and copper (I) iodide | |
| JP3659995B2 (ja) | アルキルシクロペンタジエン類の製造 | |
| JPS6357412B2 (enrdf_load_stackoverflow) | ||
| US4532020A (en) | Process for preparing a β-(fluoroalkyl or fluoroalkenyl)-β-hydroxyalkyne | |
| Yus et al. | Preparation of α, n-dilithiotoluene equivalents. Synthesis of tamoxifen | |
| Shimizu et al. | New preparation and synthetic reactions of 3, 3, 3-trifluoropropynyllithium,-borate and-stannane: facile synthesis of trifluoromethylated allenes, arylacetylenes and enynes | |
| JP3386596B2 (ja) | ５（ｅ），８（ｚ），１１（ｚ）−テトラデカトリエン−２−オンの製造方法 | |
| JP6235286B2 (ja) | （ブロモジフルオロメチル）ベンゼン誘導体及びそれらの製造方法 | |
| JP4155720B2 (ja) | 含フッ素リチオオキシラン | |
| JPH06206835A (ja) | ハロゲン化芳香族化合物の製造法 | |
| JP3722362B2 (ja) | 新規な含フッ素ケトン化合物及びその製造方法 | |
| JP3878701B2 (ja) | ４−ヒドロキシ−１−アルキン類の製造法 | |
| JP3178703B2 (ja) | オレフィンの製造方法 | |
| JP5177346B2 (ja) | α−トリフルオロメチルケトン化合物の製造方法 | |
| JP2004115377A (ja) | 含フッ素カルボン酸誘導体の製造方法 | |
| FR2604703A1 (fr) | Procede de preparation de polyfluoroenolates | |
| Hiyama et al. | Organofluorine Building Blocks | |
| JP3128967B2 (ja) | １−ブロモ−２−ヨ−ドテトラフルオロエタンの製造法 | |
| JPS6411620B2 (enrdf_load_stackoverflow) | ||
| Ward et al. | Synthesis of polyfluoroarylalkyl sulfide compounds | |
| JP4329304B2 (ja) | １，４−ジブロモブタン及びその製造方法 | |
| JP2007238527A (ja) | 含フッ素プロパルギルアルコールの製造方法 | |
| JP2024160422A (ja) | １－ハロ－２，６，１４－トリメチルオクタデカン化合物、並びにそれを用いた５，１３，１７－トリメチルアルカン化合物の製造方法 |