Acetic Acid → (+/-)-(5Z)-7-{(1R,2R,3R,5R)-5-chloro-2-[(E)-4,4-dimethyl-3-oxo-1-octenyl]-3-(tetrahydropyran-2-yloxy)-cyclopentyl}-5-heptenic acid methyl ester

HRID 1382531

반응식

HRID 1382531 반응식
[H-].[Na+].COP([CH2:9][C:10](=[O:18])[C:11]([CH3:17])([CH3:16])[CH2:12][CH2:13][CH2:14][CH3:15])(=O)OC.[CH3:19][O:20][C:21](=[O:43])[CH2:22][CH2:23][CH2:24]/[CH:25]=[CH:26]\[CH2:27][C@H:28]1[C@H:32]([Cl:33])[CH2:31][C@@H:30]([O:34][CH:35]2[CH2:40][CH2:39][CH2:38][CH2:37][O:36]2)[C@@H:29]1[CH:41]=O.C(O)(=O)C>C(COC)OC.O1CCCC1.C(OCC)C.O>[CH3:19][O:20][C:21](=[O:43])[CH2:22][CH2:23][CH2:24]/[CH:25]=[CH:26]\[CH2:27][C@H:28]1[C@H:32]([Cl:33])[CH2:31][C@@H:30]([O:34][CH:35]2[CH2:40][CH2:39][CH2:38][CH2:37][O:36]2)[C@@H:29]1/[CH:41]=[CH:9]/[C:10](=[O:18])[C:11]([CH3:16])([CH3:17])[CH2:12][CH2:13][CH2:14][CH3:15]

참가 물질

9

반응물 4

HCID 176Acetic AcidHCID 24758Sodium hydrideHCID 11234130methyl (5Z)-7-[(1R,2R,3R,5R)-5-chloro-2-formyl-3-(tetrahydro-2H-pyran-2-yloxy)cyclopentyl]-5-heptenoateHCID 13018035Dimethyl (3,3-dimethyl-2-oxoheptyl)phosphonate

생성물 1

HCID 13853246(+/-)-(5Z)-7-{(1R,2R,3R,5R)-5-chloro-2-[(E)-4,4-dimethyl-3-oxo-1-octenyl]-3-(tetrahydropyran-2-yloxy)-cyclopentyl}-5-heptenic acid methyl ester수율 61.4%

시약·촉매·용매 4

HCID 962Water용매HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매HCID 80711,2-Dimethoxyethane용매2회

반응 조건

온도
-20 °C

실험 절차

294 mg of 55% sodium hydride is suspended in 25 ml of dimethoxyethane, and 1.53 g of 3,3-dimethyl-2-oxoheptanephosphonic acid dimethyl ester is instilled. It is stirred for another 30 minutes, cooled to -20° C., and a solution of 1.98 g of VII in instilled in 10 ml of dimethoxyethane and 10 ml of tetrahydrofuran. After 1 hour it is allowed to warm to room temperature, mixed with 0.5 ml of glacial acetic acid, diluted with 200 ml of diethyl ether, shaken three times with 20 ml of salt water each, dried over magnesium sulfate and evaporated in a vacuum to dryness. The residue is chromatographed on silica gel with hexane/5-25% diethyl ether. 1.62 g of VIII is obtained as colorless oil. IR: 2998, 2955, 2863, 1730, 1684, 1621, 1437, 1060, 978/cm.

후처리

  1. waitAfter 1 hour it is allowed
  2. temperatureto warm to room temperature
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in a vacuum to dryness
  5. customThe residue is chromatographed on silica gel with hexane/5-25% diethyl ether

출처 및 근거

ORD 기록
ord-48d6969b3e31458bb371923dbbf040b3
출처 데이터셋
uspto-grants-1989_02
특허 번호
US04806668

연결된 노트

불러오는 중…