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

Participants

Reaction Conditions

Reaction Steps

To a methanol (50 mL) solution of 1,4-dioxa-spiro[4.5]decan-8-one (5 g, 32 mmol) at 0° C. was added NaBH4 (1.34 g, 35.3 mmol) in 4 portions. The solution was stirred at 0° C. for 15 min followed by stirring at room temperature for 1 hour. The methanol was evaporated and the residue partitioned between ether and water. The organic layer was separated, dried over Na2SO4 and concentrated to give the desired alcohol as a colorless oil (4.92 g). LC-MS (C8H14O3 calculated 158) m/z 159 (M+H); 1H NMR (300 MHz, CDCl3) δ 3.90 (s, 4H), 3.77 (m, 1H), 1.82 (m, 4H), 1.55 (m, 4H).

Provenance & Evidence