Benzyl Bromide → 6-((Benzyloxy)methyl)-1,4-dioxaspiro[4.5]decane

Participants

Reaction Steps

A solution of 1,4-dioxaspiro[4.5]decan-6-ylmethanol (2.3 g, 13.3 mmol) in THF (20 mL) and cooled in an ice bath, was treated with a NaH (0.48 g, 20.0 mmol). The reaction mixture was stirred for 1 hour and then benzyl bromide (2.4 mL, 20 mmol) in THF (5 mL) was added dropwise. The reaction was stirred at rt for 5 hours and then diluted with ethyl acetate (100 mL). The organic layer was washed with water, brine and dried over sodium sulfate and concentarted. Purification by silica chromatography using hexane-Et2O 20% linear gradient afforded the title compound as pale yellow solid. MS m/z 263.2 (M+1).

Provenance & Evidence