Benzyl Bromide → HCID 86760327, compound

Participants

Reaction Conditions

Reaction Steps

NaH (12 mg, 0.49 mmol, 2 eq) is added to a solution of (2S,3S,4R,5R,6S,8Z,10S,11R,12S)-5,11-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3,13-bis[(4-methoxyphenyl)methoxy]-2,4,6,8,10,12-hexamethyl-8-tridecen-1-ol (200 mg, 0.245 mmol, 1 eq) in DMF (3 mL) at −78° C. The reaction is slowly warm to 23° C. and is stirred for 1 h. Benzyl bromide (84 mg, 0.49 mmol, 2 eq) and potassium iodide (cat. 1 mg) are added and stirred for 18 h. The solvent is removed. The crude product is chromatographed (from hexane to 10% EtOAc in hexane) to give 204 mg (80%) of the desired compound as a colorless oil.

Provenance & Evidence