tert-Butanol → HCID 54210642, compound

Participants

Reaction Steps

Lithium (0.17 g, 24 mmol) was added in portions to a stirred solution of benzonitrile (0.99 mL, 1.0 g, 9.7 mmol) and t-BuOH (0.93 mL. 0.72 g, 9.7 mmol) in NH3 (50 mL) and THF (10 mL) under N2 at −78° C. After stirring for 15 minutes, benzyl-2-bromoacetate (3.1 mL, 4.5 g, 20 mmol) was added dropwise. After 1 hour, ammonium chloride (4.0 g, 75 mmol) was added in portions. The reaction mixture was slowly warmed to room temperature while the NH3 was removed with a stream of N2. Water (25 mL) was added, and the mixture extracted with EtOAc (3×5 mL). The combined organic extracts were washed with brine (50 mL), dried (MgSO4), and concentrated under reduced pressure. Flash chromatography (SiO2, 1:1-3:1 CH2Cl2:hexane) afforded 1.79 g (73%) of product as an oil.

Provenance & Evidence