Imidazole → 4-(Tert-butyldimethylsilyloxymethyl)pyridine

Participants

Reaction Steps

4-Pyridylcarbinol (8.5 g, 0.08 mol) was dissolved in a 9:1 mixture of N,N-dimethylformamide and dichloromethane (150 mL). t-Butyldimethylsilylchloride (13 g, 0.09 mol) and imidazole (6.4 g, 0.09 mol) were added and the solution was stirred for 12 hours at room temperature. The reaction mixture was concentrated at reduced pressure and the residue was partitioned between ethyl acetate and water. The organic layer was separated, dried over anhydrous magnesium sulphate, filtered and concentrated at reduced pressure to give the title compound (17.4 g, 92%) as a colorless oil; MS(ES) m/e 244 [M+H]+.

Provenance & Evidence