Dimethylformamide → Dibenzyl ether

Participants

Reaction Conditions

Reaction Steps

To a slurry of 1.44 g of prewashed sodium hydride (50% dispersion in mineral oil, 27.0 mmole, 1.6 eq.) in 20 ml of dry DMF at 0° C. was added a solution of 3.85 g title A (5) alcohol (27.0 mmole) in 10 ml DMF. The mixture was stirred at 25° C. for 15 minutes, cooled to 0° C. and then 4.3 g of benzylbromide (27.0 mmole, 1.0 eq.) was added. After stirring for 30 minutes at 25° C., the reaction mixture was poured into 300 ml of a saturated aqueous ammonium chloride solution and extracted with three 100 ml of water, dried over anhydrous MgSO4 and concentrated. The residue was purified on an LPS-1 silica gel column, eluting with 10% EtOAc/hexanes to give 4.5 g of title benzylether as a yellow oil.

Provenance & Evidence