Water → 1,4-Dioxaspiro(4.5)decan-8-ol

Participants

Reaction Conditions

Reaction Steps

A stirred, cooled (5° C.) solution of 1,4-dioxaspiro[4.5]decan-8-one (20 g, 0.128 mol) in ethanol (250 ml) was treated with sodium borohydride (7.3 g, 0.192 mol) in portions over 20 minutes. The reaction mixture was stirred at 5° C. for 1 hour then at room temperature for 1 hour. Water (20 ml) was added and the mixture was stirred vigorously for 10 minutes then concentrated in vacuo. The residue was partitioned between water (100 ml) and ethyl acetate (100 ml). The organic layer was separated and the aqueous re-extracted with ethyl acetate (100 ml). The combined organics were dried (sodium sulphate) then evaporated to give the title alcohol as a colourless oil (17.1 g, 84%). MS ES+, m/z=159 for (M+H)+; δ(360 MHz, CDCl3) 1.52-1.71 (4H, m), 1.78-1.92 (4H, m), 3.76-3.83 (1H, m), 3.91-3.94 (4H, m).

Provenance & Evidence