Dicyclohexylcarbodiimide → Cannabidiol (t-butyldimethylsilyloxy)acetate

Participants

Reaction Steps

To a stirred solution of cannabidiol (125.8 mg, 0.4 mmol) and (t-butyldimethylsilyloxy)acetic acid (112.9 mg, 0.51 mmol) in dry dichloromethane (1 mL) was added of 4-dimethylaminopyridine (6.2 mg, 0.03 mmol) followed by N,N′-dicyclohexylcarbodiimide (123.8 mg, 0.6 mmol). The mixture was stirred at ambient temperature for 1 h. Additional amounts of the acid (26.6 mg) and N,N′-dicyclohexylcarbodiimide (31 mg) were added and stirring was continued for 1 h. Mixture was diluted with hexane (2 mL), filtered, and concentrated. The crude product was purified by preparative reverse phase HPLC (C8 column) with acetonitrile-water to afford cannabidiol (t-butyldimethylsilyloxy)acetate as an oil.

Provenance & Evidence