tert-Butanol → HCID 18620044, compound

Participants

Reaction Conditions

Reaction Steps

Lithium (0.87 g, 125 mmol) was added in portions to a stirred solution of benzonitrile (5.1 mL, 5.2 g, 50 mmol) and t-BuOH (4.8 mL, 3.7 g, 50 mmol) in THF (5 mL) and NH3 (25 mL). After stirring at −78° C. for 30 minutes, a solution of bromoacetic acid ammonium salt (prepared by mixing bromoacetic acid [13.90 g, 100.0 mmol], THF (15 mL), and N2 (50 mL) at −78° C. and stirring for 1.5 hours) was added dropwise to the reaction. After stirring at −78° C. for 1 hour, ammonium chloride (20.9 g, 391 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 (75 mL) was added, and the mixture extracted with MTBE (3×50 mL). The stirred aqueous layer was cooled to 0-5° C. acidified to pH=1 with 37% HCl, and extracted with MTBE (3×50 mL). The combined organic extracts of the acidified aqueous layer were dried (MgSO4) and concentrated under reduced pressure to afford 2.49 g (31%) of product as a white solid.

Provenance & Evidence