Acetic Anhydride → (2Z)-4-{[tert-butyl(dimethyl)silyl]oxy}-2-[4-(methylsulfonyl)phenyl]-3-phenylbut-2-enyl acetate

Participants

Reaction Steps

To a solution of 46 g of (2Z)-4{[tert-butyl(dimethyl)silyl]oxy}-2-[4-(methylsulfonyl)phenyl]-3-phenylbut-2-en-1-ol with 120 mmol of DMAP in 1 L of dichloromethane, 120 mmol of acetic anhydride was added dropwise. The resulted mixture was stirred at rt for 1 h. The reaction mixture was loaded on a silica gel column and eluted with EtOAc to afford 50.5 g of the titled compound as a white solid. 1H NMR (acetone-d6, 500 MHz): δ 7.68 (d, 2H), 7.33 (d, 2H), 7.15-7.04 (m, 5H), 5.16 (s, 2H), 4.75 (s, 2H), 3.02 (s, 3H), 1.92 (s, 3H), 0.81 (s, 9H), −0.03 (s, 6H).

Provenance & Evidence