Dimethyl Sulfoxide → (S)-2-Dibenzylamino-propionaldehyde

Participants

Reaction Conditions

Reaction Steps

To a cold (−78° C.) solution of (COCl)2 (2M in CH2Cl2, 2.47 mL, 4.94 mmol) in CH2Cl2 (8 mL), DMSO (0.70 mL, 9.89 mmol) was added dropwise. After stirring at −78° C. for 15 min, a solution of (S)-2-(N,N-dibenzylamino)-1-propanol (1.01 g, 3.96 mmol) in CH2Cl2 (10 mL) was added dropwise. The mixture was stirred at −78° C. for 1 h, and then Et3N (2.76 mL, 19.78 mmol) was added. The reaction was warmed up to 0° C. and stirred for 15 min, followed by the addition of NH4Cl (25 mL, sat. aq.). The crude was extracted with CH2Cl2 (3×25 mL), washed successively with NaHCO3 (50 mL, sat. aq.) and brine (50 mL), dried over Na2SO4 and concentrated in vacuo. Aldehyde 4 was obtained as a yellow oil and used without further purification (928 mg, 93% yield).

Provenance & Evidence