Cyanic acid → Dibenzyl ether

Participants

Reaction Steps

To a slurry of 1.1 g of sodium hydride (21 mmole, 50% oil dispersion in 25 ml of dry DMF at 0° C. was added a solution of 3.34 g of title F cyanoalcohol (20 mmole) in 10 ml of DMF over a period of 10 minutes. After stirring for an additional 15 minutes, 3.6 g of benzyl bromide was added dropwise. The reaction mixture was stirred for 30 minutes at 0° C. and 3 hours at 25° C. then quenched with a saturated ammonium chloride solution, and diluted with ether. The organic layer was washed with brine. The combined aqueous layer was re-extracted with ether. The combined organic layer was dried over anhydrous MgSO4 and concentrated to leave an oil. The crude oil was chromatographed on a silica gel column, eluting with 10-20% ethyl acetate in hexanes to give 4.43 g of the title G benzyl ether.

Provenance & Evidence