Dimethyl Sulfoxide → HCID 10944542, compound

Participants

Reaction Steps

Under anhydrous conditions, dry dimethylsulfoxide (3.23 mL, 45.5 mmol) was added dropwise over a 10 min period to a stirred solution of oxalyl chloride (2.52 mL, 28.9 mmol) in dry CH2Cl2 (155 mL) at -78°. After another 10 min, a solution of (S)-2-Benzyloxy-3-phenylpropanol (5.00 g, 20.7 mmol) in CH2Cl2 (52 mL) was added dropwise over 20 min to the preceding solution at -78°. [(S)-2-Benzyloxy-3-phenylpropanol is prepared from the commercially available (S)-2-hydroxy-3-phenylpropionic acid by benzylation followed by lithium aluminium hydride reduction.] The resultant mixture was stirred at -78° for 30 min. Thereafter, triethylamine (14.41 mL, 103.3 mmol) was added rapidly to the mixture. The resulting mixture was diluted with H2O and extracted with EtOAc. The EtOAc extract was washed sequentially with a saturated aqueous solution of NH4Cl, water and brine, dried (MgSO4) and evaporated to dryness to give (S)-2-Benzyloxy-3-phenylpropanal.

Provenance & Evidence