Dimethyl Sulfoxide → 2,2-Dimethylhept-4-ynal

Participants

Reaction Conditions

Reaction Steps

To a solution of oxalyl chloride (27 g, 214 mmol) in anhydrous DCM (300 ml) at −78° C. under nitrogen was added anhydrous DMSO (33.4 g, 428 mmol) and the mixture was stirred at −78° C. for 20 min. A solution of 2,2-dimethylhept-4-yn-1-ol (20 g, 142 mmol) in anydrous DCM (50 ml) was added slowly over a period of 25 min. The reaction mixture was stirred at −78° C. for 2 hours and quenched by the addition of TEA (165 ml, 1.14 mol) and diluted with water (700 ml). The organic layer was separated and washed with a 1.5M aqueous solution of HCl (200 ml), water and brine. The organic layer was dried (MgSO4) and the solvent was removed under reduced pressure to afford the titled compound as a pale brown liquid (16.5 g, 87%). TLC: Pet. ether/EtOAc (8/2): Rf=0.75.

Provenance & Evidence