Benzyl Bromide → 2-(benzyloxymethyl)-3,4-dihydro-2H-pyran

Participants

Reaction Steps

3,4-Dihydro-2H-pyran-2-ylmethanol (5.0 g) was dissolved in tetrahydrofuran (100 ml). 55% Sodium hydride (2.3 g) and benzyl bromide (8.2 g) were added under ice-cooling, followed by stirring for 17 hours. A saturated aqueous ammonium chloride solution was added, followed by extraction with ethyl acetate and washing with brine. The organic layer was dried over anhydrous sodium sulfate and then the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (developed with ethyl acetate-hexane) to give the title compound (8.5 g) as a pale yellow oil.

Provenance & Evidence