Acetyl chloride → HCID 15538830, compound

Participants

Reaction Conditions

Reaction Steps

Alkene 1b (200 mg, 0.85 mmol) was dissolved in 20 mL of dry methylene chloride with 0.3 mL of anhydrous pyridine. The flask was purged with argon and cooled in an ice bath. Acetyl chloride (0.115 g, 1.47 mmol) in 5 mL of dry methylene chloride was added dropwise over one hour. TLC analysis (silica, 20% ethyl acetate/hexane) indicated the reaction to be complete after 2.5 hours of stirring at 0° C. The solvents were evaporated and the residue dissolved in ethyl acetate. The solution was washed four times with water, dried over MgSO4 and evaporated. The residue was purified by column chromatography on silica gel, eluting with 10-20% ethyl acetate/hexane yielding 220 mg (93%) of 1c: 1H NMR (CDCl3) δ 7.37-6.99 (m, 4H), 3.19 (s, 3H), 2.47 (sept, 1H, J=6.9 Hz), 2.33 (sept, 1H, J=6.9 Hz), 2.29 (s, 3H), 1.24 (d, 6H, J=6.9 Hz), 0.93 (d, 6H, J=6.9 Hz); 13C NMR (CDCl3) δ 169.46, 150.62, 149.03, 139.02, 133.64, 128.95, 127.24, 122.89, 120.72, 56.50, 30.49, 26.98, 22.06, 21.25, 21.05.

Provenance & Evidence