Ethyl Acetate → Hexahydro-2-oxo-4-(5-phenyl-3-oxo-1E-pentenyl)-cyclopenta[b]furan

HRID 375595

반응식

HRID 375595 반응식
COP([CH2:7][C:8](=[O:17])[CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)(=O)OC.[OH-].[Na+].[C:20]([O:23][CH2:24][CH3:25])(=[O:22])[CH3:21]>[Cl-].C([N+](CC)(CC)CC1C=CC=CC=1)C.ClCCl>[O:22]=[C:20]1[O:23][CH:24]2[CH2:7][CH2:8][CH:9](/[CH:10]=[CH:7]/[C:8](=[O:17])[CH2:9][CH2:10][C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH:25]2[CH2:21]1

참가 물질

6

반응물 3

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 2733973Dimethyl(2-oxo-4-phenylbutyl)phosphonate

생성물 1

HCID 18993488Hexahydro-2-oxo-4-(5-phenyl-3-oxo-1E-pentenyl)-cyclopenta[b]furan

시약·촉매·용매 2

HCID 66133Benzyl triethylammonium chloride촉매HCID 6344Dichloromethane용매

실험 절차

To a solution of dimethyl(2-oxo-4-phenylbutyl)phosphonate (1.40 g, 5.46 mmol), [3aα,4β,5α]-hexahydro-2-oxo-cyclopenta[b]furan-4-carboxaldehyde (4) (0.765 mg, 4.96 mmol) and triethylbenzyl ammonium chloride (110 mg 0.48 mmol) in dichloromethane (10 mL) at room temperature was added a 10M aqueous solution sodium hydroxide (0.55 mL, 5.5 mmol) and the resulting mixture was vigorously stirred for 40 min. The reaction was then diluted with ethyl acetate and washed with water (2×10 mL) and brine (1×10 mL) and concentrated in vacuo. Column chromatography (1:2 ethyl acetate-hexanes through silica gel) provided the title compound 5 as a clear, colorless oil (1.29 g, 4.53 mmol). Rf =0.42 in ethyl acetate-hexanes, 1:1.

후처리

  1. washwashed with water (2×10 mL) and brine (1×10 mL)
  2. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-ab4c9de3c96148dba114727323ef4fb6
출처 데이터셋
uspto-grants-1996_01
특허 번호
US05486540

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