1,4-Dioxaspiro[4.5]decan-8-one → 1,4-Dioxaspiro(4.5)decan-8-ol

Participants

Reaction Steps

A solution of 1,4-dioxaspiro[4.5]decan-8-one (20.40 g, 130.60 mmol) in anhydrous methanol (200 mL) at 0° C., under nitrogen, was treated with sodium borohydride (2.50 g, 65.30 mmol), portion wise. The resulting mixture was stirred for 24 hours and concentrated in vacuo to dryness. The residue was diluted with ethyl acetate (300 mL), washed with 1 M hydrochloric acid (3×100 mL), brine (3×100 mL), dried over anhydrous sodium sulfate and concentrated in vacuo to afford the title compound as a colorless oil (11.2 g, 51%): 1H NMR (300 MHz, CDCl3) δ 3.91-3.87 (m, 4H), 3.79-3.70 (m, 1H), 1.92 (br s, 1H), 1.89-1.71 (m, 4H), 1.67-1.47 (m, 4H); MS (ES+) m/z 140.9 (M-OH).

Provenance & Evidence