Water → 8-[2-(Benzyloxy)ethyl]-1,4-dioxaspiro[4.5]decane

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Reaction Steps

To a mixture of NaH (60% in oil, 43.6 g, 1.09 mol) in DMF (900 mL) is carefully added crude 2-(1,4-dioxaspiro[4.5]dec-8-yl)ethanol (139.5 g) in DMF (300 mL) at 0-5° C., and the mixture is stirred for 30 min at the same temperature. To the mixture is added dropwise benzyl bromide (129.6 mL, 1.09 mol) at 0-5° C., and stirring is continued for 1 hour at the same temperature. After addition of H2O (1000 mL), the mixture is extracted with EtOAc-Hexane (3:1, 1200 mL). The water layer is extracted with EtOAc-Hexane (3:1, 1200 mL×2), and the combined organic layer is washed with brine, dried over magnesium sulfate, and concentrated under reduced pressure to afford crude 8-[2-(benzyloxy)ethyl]-1,4-dioxaspiro[4.5]decane. The crude product is used without further purification.

Provenance & Evidence