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

HRID 375595

反応式

HRID 375595 の反応式
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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 66133Benzyl triethylammonium chloride触媒HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-ab4c9de3c96148dba114727323ef4fb6
出典データセット
uspto-grants-1996_01
特許番号
US05486540

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