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

HRID 375595

Reaction equation

HRID 375595 reaction equation
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

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-ab4c9de3c96148dba114727323ef4fb6
Source dataset
uspto-grants-1996_01
Patent number
US05486540

Linked notes

Loading…