Acetic Anhydride → HCID 9943807, compound

Participants

Reaction Steps

To a mixture of 10 mg of indole 1b (0.04 mmole), 5 mg (0.04 mmole) dimethylaminopyridine (DMAP) in 5 ml of chloroform, was added 100 mg of acetic anhydride. The reaction was stirred at room temperature for 25 min and then added directly to a silica gel chromatography column employing chloroform as the eluant. The purified indole 1c was recrystallized from chloroform/hexane: 11 mg (95%) yield; mp 210-212° C.; TLC (chloroform/methanol, 90:10) Rf=0.68; 1HNMR (CDCl3) δ 9.38 (1H, bs, indole proton), 5.03 (2H, s, 2-methylene), 2.32 (4H, s, ethylene), 2.31 (3H, s, 3-methyl) 2.08 and 2.05 (6H, 2s, methyls); IR (KBr pellet) 3207, 2924, 1734, 1664, 1624, 1566, 1500, 1361, 1350, 1242, 1209, 1155, 1020, 962, 817, 781 cm−1; MS (EI mode) m/z 288 (M+), 245 (M+-CH3—C═O), 228, 213, 201, 185. Anal. Calcd (C15H16N2O4) C, H, N.

Provenance & Evidence