Acetic Acid → 5-Hydroxy-hexahydro-pentalen-2-one

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Reaction Steps

1.1 g of sodium borohydride (0.029 mol) is added with stirring to a solution of 11.6 g of bicyclo[3.3.0]octane-3,7-dione (8.4×10-2 mol) in 100 ml of methylene chloride and 100 ml of ethanol. After 45 minutes at this temperature, the excess reagent is decomposed by slowly adding 20 ml of acetone. The mixture is then neutralized with 1.4 ml of acetic acid, and evaporated under vacuum to afford a residue which is taken up in water and methylene chloride. The organic phase is evaporated to dryness and filtered on silica gel (70:30 hexane:ethyl ether as eluent) to afford 9.1 g of 7ξ-hydroxy-bicyclo[3.3.0]octan-3-one.

Provenance & Evidence