Dimethyl Sulfoxide → 3-(Pyridin-2-YL)propanal

Participants

Reaction Conditions

Reaction Steps

35 ml (0.41 mol) of oxalyl chloride were dissolved in 700 ml of dry DCM and cooled to −70° C. A mixture of 62 ml (0.87 mol) of DMSO and 40 ml of dry DCM was added dropwise to this solution over a period of 25 min. During this, the temperature was kept strictly below −65° C. (exothermic reaction). After stirring at −70° C. for 15 min, 50 g (0.36 mol) of freshly distilled 3-(2-pyridyl)propanol dissolved in 150 ml of dry DCM were added dropwise at below −65° C. over a period not exceeding 15 min. 218 ml (0.37 mol) of TEA were added in 40 min, and then the mixture was slowly warmed to RT. 190 ml of water were added to dissolve the salts which had formed. The phases were separated, the DCM phase was concentrated in vacuo, and the product was then purified by distillation (2 mbar, 59-70° C.).

Provenance & Evidence