2-(5-Methoxyhept-1-yl)bicyclo[3.3.0]octan-7-one hexahydro-4-(5-methoxyheptyl)-2(1H)-pentalenone → 2-(5-Methoxyhept-1-yl)-7-methyl-bicyclo[3.3.0]octan-7-ol

HRID 1789535노트

반응식

HRID 1789535 반응식
[CH3:1][O:2][CH:3]([CH2:17][CH3:18])[CH2:4][CH2:5][CH2:6][CH2:7][CH:8]1[CH2:15][CH2:14][CH:13]2[CH:9]1[CH2:10][C:11](=[O:16])[CH2:12]2.[CH3:19]OC(CC)CCCCC1CCC2C1CC(=O)C2.C([Mg]Br)C>CCOCC>[CH3:1][O:2][CH:3]([CH2:17][CH3:18])[CH2:4][CH2:5][CH2:6][CH2:7][CH:8]1[CH2:15][CH2:14][CH:13]2[CH:9]1[CH2:10][C:11]([CH3:19])([OH:16])[CH2:12]2

참가 물질

4

반응물 2

HCID 201884142-(5-Methoxyhept-1-yl)bicyclo[3.3.0]octan-7-one hexahydro-4-(5-methoxyheptyl)-2(1H)-pentalenoneHCID 178418443HCID 178418443, 화합물

생성물 1

HCID 150530092-(5-Methoxyhept-1-yl)-7-methyl-bicyclo[3.3.0]octan-7-ol수율 39.9%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매2회

실험 절차

2-(5-Methoxyhept-1-yl)bicyclo[3.3.0]octan-7-one hexahydro-4-(5-methoxyheptyl)-2(1H)-pentalenone, (4 g, 0.0158 moles) diluted in ether is added dropwise to a stirring solution of ethyl magnesium bromide (0.0158 moles) dissolved with diethyl ether. The mixture is cooled in an ice bath during the addition. The ice bath is removed and the solution stirred for an additional hour. The reaction is quenched with water and a 15% sulfuric acid solution. The organic phase is separated and the solvent removed under vacuum. The aqueous layer is extracted (2×200 ml) and the extracts are combined with the organic layer and dried over anhydrous sodium sulfate. The solid is filtered off and the remaining solvent removed leaving a clear, pale yellow oil. The crude product is subsequently chromatographed on silica gel yielding desired product as a clear colorless oil (1.7 g, 6.3 mmoles).

후처리

  1. temperatureThe mixture is cooled in an ice bath during the addition
  2. customThe ice bath is removed
  3. customThe reaction is quenched with water
  4. customThe organic phase is separated
  5. customthe solvent removed under vacuum
  6. extractionThe aqueous layer is extracted (2×200 ml)
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationThe solid is filtered off
  9. customthe remaining solvent removed
  10. customleaving a clear, pale yellow oil

출처 및 근거

ORD 기록
ord-3b4f3d8c616a4a45ba2bbc193e565046
출처 데이터셋
uspto-grants-1987_08
특허 번호
US04689349

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