Benzyl Bromide → HCID 131720909, compound

Participants

Reaction Steps

To a solution of methyl α-L-fucopyranoside (1.96 g, 9.61 mmol; Aldrich, Sigma), BnBr (8 mL, 67.3 mmol; benzyl bromide), and TBAI (177 mg, 048 mmol; tetrabutylammonium iodide; Aldrich) in THF (20 mL; tetrahydrofuran) at 0° C. was added NaH (2.35 g, 57.6 mmol). The cooling bath was removed and the reaction mixture was allowed to stir for 24 h. The reaction was diluted with EtOAc (50 mL; ethyl acetate) and poured into a saturated NH4Cl solution (50 mL). The aqueous phase was extracted with EtOAc (2×30 mL) and the combined organic phases were dried (MgSO4) and concentrated under reduced pressure providing the crude oil. Purification by silica gel flash chromatography (hexane:EtOAc, 100% to 9:1 to 1:1) gave the desired product in excellent yield (5.0 g, 92%).

Provenance & Evidence