2-(Dimethylamino)ethanol → F2158-1258

Participants

Reaction Steps

To a suspension of solid-supported triphenylphosphine (30.0 g, 30.0 mmol) in DCM (150 mL) was added DEAD (3.93 mL, 25.0 mmol) dropwise via a syringe at room temperature. The reaction mixture was stirred for 1 hr, and then a solution of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenol (4.40 g, 20.0 mmol) and 2-(dimethylamino) ethanol (2.01 mL, 20.0 mmol) in DCM (30 mL) was introduced. The reaction mixture was stirred at room temperature for 2 days. The mixture was filtered and the filtrate was concentrated. The residue was purified by silica gel column chromatography (eluting with 95:5, DCM/MeOH) to afford 4-dimethylaminoethoxyphenyl boronic acid, pinacol ester (2.25 g) as an yellow oil. MS (MH+) 292.4; Calculated 29 for C16H26BNO3

Provenance & Evidence