Acetyl chloride → HCID 388025, compound

Participants

Reaction Steps

Acetyl chloride (1.1 g, 13.6 mmol) was added to a solution of 10 (2.0 g, 7.4 mmol) in 1,2-dichloroethane (100 mL) and the mixture was refluxed for 4 h. After this time, the solution was poured into ice water. The organic layer was separated, washed with saturated NaHCO3 and water, dried, and evaporated. The residue was subjected to column chromatography (silica gel, C6H6) to give 11 as a yellow solid (mp 174-176° C.) in a 74% yield: IR (KBr) 1645, 1655, 1724 (C═O) cm−1; 1H NMR (CDCl3) δ 1.68 (d, J=6.6 Hz, 3H, CHCH3), 2.13 (s, 3H, COCH3), 6.10-6.17 (q, J=6.6 Hz, 1H, CH), 7.53 (s, 1H, H-3), 7.63 (d, J=5.1 Hz, 1H, H-7), 7.68 (d, J=5.1 Hz, 1H, H-6); 13C NMR (CDCl3): δ 21.0 (C-2-COCH3), 22.0 (C-2-CHCH3), 67.4 (C-2-CH), 123.4 (C-3), 126.6 (C-7), 133.6 (C-6), 154.0 (C-2), 174.4×2 169.8 (C-2-C═O), (C-4, C-8); MS m/z 306 (M+); Anal. (C14H10O4S2) C, H.

Provenance & Evidence