Imidazole → 3-(Tert-butyldiphenylsilyloxy)propanenitrile

Participants

Reaction Steps

3-Hydroxyproprionitrile (7.11 g, 100 mmol) and imidazole (68.08 g, 100 mmol) in dry THF (100 ml) was stirred at room temperature for 45 mins and tert-butyldiphenylsilylchloride (28.86 g, 105 mmol) was added slowly by syringe over 10 mins. The clear solution was stirred at room temperature overnight during which time a white precipitate formed. The reaction was filtered and the filtrate evaporated in vacuo to leave an oil which was chromatographed on silica (eluting with 10% petrol in ether) to give the product as a clear slightly yellow oil (31.41 g, quant.) δH (CDCl3) 7.76-7.65 (4H, m, PhH4), 7.48-7.35 (6H, m, PhH6), 3.86 (2H, t, J 6.5, OCH2CH2CN), 2.54 (2H, t, J 6.5, OCH2 CH2CN), 1.09 (9H, s, tert-Bu).

Provenance & Evidence