Benzyl Bromide → HCID 86714024, compound

Participants

Reaction Steps

To a solution of tetraol (13, 8.4 g, 18 mmol) from Step 2 in N,N-dimethylformamide (100 mL) at 0° C. under an atmosphere of nitrogen was added sodium hydride (60% dispersion in mineral oil, 10.1 g, 252 mmol), and the mixture was stirred for 30 min at the same temperature. Then benzyl bromide (19.5 mL, 162 mmol) was added dropwise, and the mixture was stirred with gradual warming to ambient temperature over 5 h. After re-cooling to 0° C., the reaction mixture was quenched by addition of water (100 mL). The mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate, filtered and evaporated in vacuo. The resulting crude residue was purified on a Biotage® purification apparatus (silica gel, 5 to 20% tetrahydrofuran in hexanes gradient) to yield the title compound (19, 14.8 g, 18 mmol, 100%) as a white solid.

Provenance & Evidence