Dimethyl Sulfoxide → HCID 131725264, compound

Participants

Reaction Conditions

Reaction Steps

Using the method of Swern, et al., N-(2-{[3-(2,4-dichlorophenyl)-4-(hydroxymethyl)phenyl]amino}ethyl)(tert-butoxy)carboxamide (100 mg) is dissolved in anhydrous methylene chloride (1 ml) and added to a premixed solution of oxalyl chloride (1.5 eq) and DMSO (3 eq) in methylene chloride (25 ml) which has been stirring at −78° C. for 15 min. The resulting solution is stirred at −78° C. for an additional 30 min, at which time triethyl amine (6 eq) is added. The resulting suspension is allowed to warm to room temperature. After 15 min., water (1 ml) is added and the layers separated. The aqueous layer is extracted with methylene chloride (2×10 ml), and the combined organic layers dried (sodium sulfate) and concentrated to afford aldehyde 8 in 70–80% yield as a light yellow foam. This product proves to be unstable and is used without further manipulation.

Provenance & Evidence