Benzyl Bromide → 6-(Benzyloxy)hexahydrofuro[3,2-b]furan-3-ol

Participants

Reaction Conditions

Reaction Steps

To a solution of sodium hydride (3.24 g, 81.0 mmol) in anhydrous DMF (20 mL) was added hexahydrofuro[3,2-b]furan-3,6-diol (10.1 g, 69.1 mmol) at 0° C. and the mixture was stirred for 1 h at 0° C. To the mixture was added bromomethylbenzene (11.73 g, 68.58 mmol) and the resulting mixture was stirred at rt for 4.5 h, and then quenched with H2O 2O (50 mL). The separated water layer was extracted with EtOAc (250 mL×3). The combined organic layers were washed with H2O (50 mL×6), dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography (PE/EtOAc (v/v)=2/1) to give the title compound as light yellow oil (8.1 g, 50%).

Provenance & Evidence