Imidazole → HCID 131735123, compound

Participants

Reaction Steps

To a solution of 4-cyanobenzyl alcohol (5.0 g, 37.9 mmol) in DMF was added imidazole (2.79 g, 41 mmmol) and tert-butyldimethylsilyl chloride (6.2 g, 41 mmol). After stirring for 14 h, the reaction mixture was poured into 0.1M aqueous KHSO4 and extracted three times with diethyl ether. The combined organic phases were washed twice with water, once with brine and dried over MgSO4. Filtration followed by removal of volatiles under reduced pressure gave crude product. Flash chromatography (10% EtOAc in hexane) provided 4-(tert-butyl-dimethyl-silanyloxymethyl)-benzonitrile as a white solid (3.41 g, 36%). 1H NMR (300 MHz, CDCl3) δ ppm 7.57 (d, 2H), 7.36 (d, 2H), 4.68 (d, 2H), 0.82 (s, 9H), 0.02 (2, 6H).

Provenance & Evidence