2-[2-[tert-butyl(dimethyl)silyl]oxyphenyl]acetonitrile

Conditions: temp:35.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Mandelonitrile (50 g, 0.38 moles) and imidazole (64 g, 0.94 moles) were dissolved in DMF (100 cm3) and the resulting solution cooled in an ice-water bath. tert-Butyldimethylsilyl chloride (68 g, 0.45 moles) was then added portionwise over a period of 20 minutes. The flask contents were then warmed to 35° C. and stirred at that temperature for 18 hours. The reaction mixture was then cooled and partitioned between ethyl acetate (3×100 cm3) and deionised water (100 cm3). The combined organic fractions were then washed with brine (100 cm3), dried over anhydrous magnesium sulphate and concentrated under reduced pressure to give the crude product as a yellow oil. Flash chromatography (600 g kieselgel 60 silica) eluting with 20% dichloromethane in pentane gave the title compound as an oil (77 g, 0.31 moles, 82%), δH (300 MHz;CDCl3) 0.1 (3H, s), 0.2 (3H, s), 1.0 (9H, s), 5.5 (1H, s), and 7.4 (5H, m). the resulting solution cooled in an ice-water bath The reaction mixture was then cooled partitioned between ethyl acetate (3×100 cm3) and deionised water (100 cm3) The combined organic fractions were then washed with brine (100 cm3) dried over anhydrous magnesium sulphate concentrated under reduced pressure to give the crude product as a yellow oil Flash chromatography (600 g kieselgel 60 silica) eluting with 20% dichloromethane in pentane