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

Participants

Reaction Steps

Into a 500-mL 3-necked round-bottom flask was placed 1,4-dioxaspiro[4.5]decan-8-one (20 g, 128.06 mmol, 1.00 equiv), methanol (250 mL) and NaBH4 (7.3 g, 198.23 mmol, 1.55 equiv). The resulting solution was stirred for 2 h at room temperature. The reaction was then quenched by the addition of 150 mL of NH4Cl (sat., aq.). The resulting solution was extracted with 2×300 mL of ethyl acetate and the organic layers combined and dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:10). Purification afforded 19.6 g (97%) of 1,4-dioxaspiro[4.5]decan-8-ol as a colorless oil.

Provenance & Evidence