SU730304A3 - Способ получени этил-(3-оксо-транс8,9-эпокси-цис)-6-тетрадеценоата - Google Patents
Способ получени этил-(3-оксо-транс8,9-эпокси-цис)-6-тетрадеценоата Download PDFInfo
- Publication number
- SU730304A3 SU730304A3 SU752151516A SU2151516A SU730304A3 SU 730304 A3 SU730304 A3 SU 730304A3 SU 752151516 A SU752151516 A SU 752151516A SU 2151516 A SU2151516 A SU 2151516A SU 730304 A3 SU730304 A3 SU 730304A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- epoxy
- trans
- ethyl
- temperature
- oxo
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 33
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 16
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 14
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 9
- HJUGFYREWKUQJT-UHFFFAOYSA-N tetrabromomethane Chemical compound BrC(Br)(Br)Br HJUGFYREWKUQJT-UHFFFAOYSA-N 0.000 claims description 6
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 229910000104 sodium hydride Inorganic materials 0.000 claims description 3
- 239000012312 sodium hydride Substances 0.000 claims description 3
- 239000004593 Epoxy Substances 0.000 claims description 2
- 125000004494 ethyl ester group Chemical group 0.000 claims description 2
- 150000002680 magnesium Chemical class 0.000 claims description 2
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 abstract description 4
- 229910052700 potassium Inorganic materials 0.000 abstract description 4
- 239000011591 potassium Substances 0.000 abstract description 4
- BMTAFVWTTFSTOG-UHFFFAOYSA-N Butylate Chemical group CCSC(=O)N(CC(C)C)CC(C)C BMTAFVWTTFSTOG-UHFFFAOYSA-N 0.000 abstract description 3
- TVDSBUOJIPERQY-UHFFFAOYSA-N prop-2-yn-1-ol Chemical compound OCC#C TVDSBUOJIPERQY-UHFFFAOYSA-N 0.000 abstract description 3
- 150000001875 compounds Chemical class 0.000 abstract 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound 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 abstract 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 150000001408 amides Chemical class 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 abstract 1
- 150000004678 hydrides Chemical class 0.000 abstract 1
- 150000002440 hydroxy compounds Chemical class 0.000 abstract 1
- 229910052744 lithium Inorganic materials 0.000 abstract 1
- 150000002901 organomagnesium compounds Chemical class 0.000 abstract 1
- 150000003112 potassium compounds Chemical class 0.000 abstract 1
- 229910052708 sodium Inorganic materials 0.000 abstract 1
- 239000011734 sodium Substances 0.000 abstract 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 16
- 239000000047 product Substances 0.000 description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 8
- 239000000377 silicon dioxide Substances 0.000 description 8
- 239000000243 solution Substances 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 239000003921 oil Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- NOTFZGFABLVTIG-UHFFFAOYSA-N Cyclohexylethyl acetate Chemical compound CC(=O)OCCC1CCCCC1 NOTFZGFABLVTIG-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 2
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- VIHYIVKEECZGOU-UHFFFAOYSA-N N-acetylimidazole Chemical compound CC(=O)N1C=CN=C1 VIHYIVKEECZGOU-UHFFFAOYSA-N 0.000 description 1
- UGAPHEBNTGUMBB-UHFFFAOYSA-N acetic acid;ethyl acetate Chemical compound CC(O)=O.CCOC(C)=O UGAPHEBNTGUMBB-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- RWDDSTHSVISBEA-UHFFFAOYSA-N dec-2-yne Chemical compound CCCCCCCC#CC RWDDSTHSVISBEA-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 150000002118 epoxides Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- FRIJBUGBVQZNTB-UHFFFAOYSA-M magnesium;ethane;bromide Chemical compound [Mg+2].[Br-].[CH2-]C FRIJBUGBVQZNTB-UHFFFAOYSA-M 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 150000003180 prostaglandins Chemical class 0.000 description 1
- 125000002943 quinolinyl group Chemical class N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 150000003385 sodium Chemical class 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/38—Compounds containing oxirane rings with hydrocarbon radicals, substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D303/40—Compounds containing oxirane rings with hydrocarbon radicals, substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals by ester radicals
- C07D303/42—Acyclic compounds having a chain of seven or more carbon atoms, e.g. epoxidised fats
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Epoxy Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7431500A FR2285384A1 (fr) | 1974-09-18 | 1974-09-18 | Nouveau procede de preparation de trans-epoxy cis-alcenes substitues |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU730304A3 true SU730304A3 (ru) | 1980-04-25 |
Family
ID=9143194
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU752151516A SU730304A3 (ru) | 1974-09-18 | 1975-07-10 | Способ получени этил-(3-оксо-транс8,9-эпокси-цис)-6-тетрадеценоата |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US3984442A (en, 2012) |
| JP (1) | JPS5152123A (en, 2012) |
| AT (1) | AT343669B (en, 2012) |
| BE (1) | BE833416A (en, 2012) |
| CA (1) | CA1072570A (en, 2012) |
| CH (1) | CH602690A5 (en, 2012) |
| DD (1) | DD122246A5 (en, 2012) |
| DE (1) | DE2541711A1 (en, 2012) |
| DK (1) | DK415075A (en, 2012) |
| ES (1) | ES440941A1 (en, 2012) |
| FR (1) | FR2285384A1 (en, 2012) |
| GB (2) | GB1475027A (en, 2012) |
| HU (1) | HU173002B (en, 2012) |
| IE (1) | IE42014B1 (en, 2012) |
| IL (1) | IL47821A (en, 2012) |
| LU (1) | LU73397A1 (en, 2012) |
| NL (1) | NL7511039A (en, 2012) |
| SE (1) | SE411043B (en, 2012) |
| SU (1) | SU730304A3 (en, 2012) |
| ZA (1) | ZA754906B (en, 2012) |
-
1974
- 1974-09-18 FR FR7431500A patent/FR2285384A1/fr active Granted
-
1975
- 1975-07-10 SU SU752151516A patent/SU730304A3/ru active
- 1975-07-11 HU HU75RO00000845A patent/HU173002B/hu unknown
- 1975-07-22 SE SE7508333A patent/SE411043B/xx unknown
- 1975-07-25 IL IL47821A patent/IL47821A/xx unknown
- 1975-07-30 ZA ZA00754906A patent/ZA754906B/xx unknown
- 1975-08-15 US US05/605,159 patent/US3984442A/en not_active Expired - Lifetime
- 1975-09-11 JP JP50109526A patent/JPS5152123A/ja active Pending
- 1975-09-15 ES ES440941A patent/ES440941A1/es not_active Expired
- 1975-09-15 LU LU73397A patent/LU73397A1/xx unknown
- 1975-09-15 BE BE160041A patent/BE833416A/xx unknown
- 1975-09-16 DD DD188368A patent/DD122246A5/xx unknown
- 1975-09-17 IE IE2045/75A patent/IE42014B1/en unknown
- 1975-09-17 GB GB3823575A patent/GB1475027A/en not_active Expired
- 1975-09-17 GB GB1563876A patent/GB1475028A/en not_active Expired
- 1975-09-17 DK DK415075A patent/DK415075A/da not_active Application Discontinuation
- 1975-09-17 CA CA235,670A patent/CA1072570A/en not_active Expired
- 1975-09-17 CH CH1205475A patent/CH602690A5/xx not_active IP Right Cessation
- 1975-09-18 NL NL7511039A patent/NL7511039A/xx not_active Application Discontinuation
- 1975-09-18 DE DE19752541711 patent/DE2541711A1/de not_active Withdrawn
- 1975-09-18 AT AT717475A patent/AT343669B/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| IE42014B1 (en) | 1980-05-21 |
| IE42014L (en) | 1976-03-18 |
| IL47821A0 (en) | 1975-10-15 |
| IL47821A (en) | 1979-07-25 |
| SE7508333L (sv) | 1976-03-19 |
| DD122246A5 (en, 2012) | 1976-09-20 |
| NL7511039A (nl) | 1976-03-22 |
| JPS5152123A (en) | 1976-05-08 |
| FR2285384A1 (fr) | 1976-04-16 |
| GB1475027A (en) | 1977-06-01 |
| GB1475028A (en) | 1977-06-01 |
| ATA717475A (de) | 1977-10-15 |
| US3984442A (en) | 1976-10-05 |
| ES440941A1 (es) | 1977-06-01 |
| DE2541711A1 (de) | 1976-04-08 |
| CA1072570A (en) | 1980-02-26 |
| AU8322875A (en) | 1977-02-17 |
| ZA754906B (en) | 1976-09-29 |
| HU173002B (hu) | 1979-01-28 |
| AT343669B (de) | 1978-06-12 |
| LU73397A1 (en, 2012) | 1976-04-13 |
| BE833416A (fr) | 1976-03-15 |
| CH602690A5 (en, 2012) | 1978-07-31 |
| DK415075A (da) | 1976-03-19 |
| SE411043B (sv) | 1979-11-26 |
| FR2285384B1 (en, 2012) | 1978-12-29 |
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