Water → N-(4-Hydroxycyclopent-2-enyl)-benzamide

Participants

Reaction Steps

Molybdenum hexacarbonyl (12.1 g, 45.8 mmol) was added to a solution of the bicycle 7 (6.10 g, 30.3 mmol) in a 7:1 mixture of acetonitrile and water (280 cm3). The suspension was stirred for 30 minutes at room temperature, then sodium borohydride (0.60 g, 15.9 mmol) was added and the suspension was heated under reflux for 4 hours. Upon completion of reaction, the mixture was allowed to cool to room temperature, filtered though a celite plug, and evaporated to dryness to give a brown solid. Flash chromatography (SiO2, 80% ethyl acetate in petrol) gave the alcohol 8 (3.60 g, 17.7 mmol, 58%) as a light yellow solid; m/z (EI) Found [M]+ 203.0945 ([M]+ C12H13NO2 requires 203.0946).

Provenance & Evidence