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

Participants

Reaction Conditions

Reaction Steps

1,4-dioxaspiro[4.5]decan-8-one (150 g, 0.96 mol) was stirred with MeOH (1200 mL) under N2 until dissolution occurred. Cooled to −5° C. in a drykold/acetone bath and treated portionwise with NaBH4 (72.6 g, 1.82 mol) over 2hrs. (T<10° C.). On complete addition, the mixture was cooled to −10° C. and then left to warm to room temperature. Stirred overnight at room temperature. The resulting mixture was evaporated and treated with ice-cold 5N NaOH (400 mL) and extracted with CH2Cl2 (2×500 mL) followed by extraction with 4:1 dichloromethane:isopropanol (2×250 mL). The combined extracts were washed with brine (2×200 mL), dried overnight (Na2SO4) and evaporated to give a colourless oil. This was further dried in vacuo to give 1,4-dioxaspiro[4.5]decan-8-ol (141.8 g, 93% yield.)1H NMR: CDCl3 (250 MHz) 3.91 (4H, m), 3.81 (1H, m), 1.21-1.88 (8H, m, aliphatic H's).

Provenance & Evidence