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0 °C

To a stirred solution of 4-hydroxybenzyl cyanide 77 (2.0 g, 15.0 mmol) in DMF (10 ml) was added t-butyldimethylsilyl chloride (2.5 g, 16.5 mmol). The reaction mixture was cooled to 0° C. and imidazole (2.3 g, 33.0 mmol) was added and then the mixture was allowed to warm to ambient temperature. After stirring for 3 hours, the reaction mixture was diluted with ether and washed with 0.5 M HCl, sat. aq. NaHCO3, water, and brine, then dried over MgSO4. The crude product was purified via flash SiO2 (eluted with hexane/ethyl acetate (8:1)) to give 78 as a clear oil (3.6 g, 98% yield). 1H-NMR (400 MHz, chloroform-d) δ 7.87 (d, J=8.5 Hz, 2H), 6.86 (d, J=8.5 Hz, 2H), 3.54 (s, 2H), 0.98 (s, 9H), 0.23 (s, 6H).

1. temperatureto warm to ambient temperature
2. washwashed with 0.5 M HCl, sat. aq. NaHCO3, water, and brine
3. dry with materialdried over MgSO4
4. customThe crude product was purified via flash SiO2 (eluted with hexane/ethyl acetate (8:1))