Water → HCID 178437734, compound

Participants

Reaction Steps

6.7 g (86 mmol) of DMSO in 17 ml of dichloromethane were added under N2 to a solution of 5.5 g (43 mmol) of oxalyl chloride in 50 ml of dichloromethane at -78° C. After 5 minutes, a solution of 10.6 g (39 mmol) of the hydroxymethyl compound from Example 3 in 5.3 ml each of DMSO and dichloromethane was added, and the mixture was stirred for 1 hour at the temperature indicated. 35.6 g (350 mmol) of triethylamine were added dropwise. After 20 minutes, the mixture was allowed to warm to room temperature, 105 ml of H2O were added, extraction was carried out with dichloromethane, and removal of the solvent gave 9.5 g (35.5 mmol =91%) of the aldehyde as a white solid: m.p. 96° to 97° C.

Provenance & Evidence