Triethylamine → HCID 22257870, compound

Participants

Reaction Steps

At room temperature, triethylamine (2.27 ml, 16.3 mmol) and TBDMS chloride (1.65 g, 10.95 mmol) were added to a solution of 2-hydroxymethylbenzimidazole (1.48 g, 9.95 mmol) in DMF-(30 ml). After 3.5 h, the reaction-was terminated by addition of water, the mixture was extracted with diethyl ether and the organic phase was dried over sodium sulphate. Chromatography (silica gel, cyclohexane:ethyl acetate 2:1, Rf=0.35) gave 2.52 g of 2-tert-butyldimethylsilyloxymethyl-benzimidazole (97% of theory) as a brownish powder. MS (DCI, NH3)=263 (M+H+). 1H-NMR (DMSO-d6): 0.00 (6H, s); 0.80 (9H, s); 4.75 (2H, s); 7.0-7.1 (2H, m); 7.4-7.5 (2H, m); 12.15 (1H, br s).

Provenance & Evidence