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

HRID 375595

Reaktionsgleichung

Reaktionsgleichung von HRID 375595
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

Komponenten

6

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 66133Benzyl triethylammonium chlorideKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-ab4c9de3c96148dba114727323ef4fb6
Quelldatensatz
uspto-grants-1996_01
Patentnummer
US05486540

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