Acetic Anhydride → (1-Trityl-1H-imidazol-4-YL)methyl acetate

Reaction equation

[C:1]([N:20]1[CH:24]=[C:23]([CH2:25][OH:26])[N:22]=[CH:21]1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:27](OC(=O)C)(=[O:29])[CH3:28].CCOC(C)=O>N1C=CC=CC=1>[C:27]([O:26][CH2:25][C:23]1[N:22]=[CH:21][N:20]([C:1]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:24]=1)(=[O:29])[CH3:28]

Participants

Procedure

To a suspension of the title A compound 1-trityl-4-hydroxymethyl-1H-imidazole (34.5 g, 101 mmol) in pyridine (200 mL) is added acetic anhydride (28.6 mL, 303 mmol) in a dropwise fashion and the reaction is stirred until it becomes clear. The reaction mixture is poured into EtOAc and then washed with 0.5N aqueous HCl, saturated aqueous sodium bicarbonate and brine. The combined organic phases are dried over anhydrous sodium sulfate and then filtered through a silica pad yielding a solid after removal of the solvent in vacuo. The solid is triturated with diethyl ether to give 4-acetoxymethyl-1-tritylimidazole: m.p. 133-134° C.; 1H-NMR (DMSO-d6) δ 7.42 (10H, m), 7.09 (6H, m), 6.99 (1H, s), 4.89 (2H, s), 1.99 (3H, s); e/z (ES) 383 (M+1, 5%), 243 (100%).