Dimethyl Sulfoxide → HCID 15181216, compound

Participants

Reaction Steps

A solution of dimethyl sulfoxide (25.1 ml, 353 mmol) in CH2Cl2 (75 ml) was added to a stirred solution of oxalyl chloride (14.75 ml, 169 mmol) in CH2Cl2 (370 ml) at -60° C. The reaction mixture was stirred for 1 hour and a propylamino-solution of 6-diisopropylaminohex-4-yn-1-ol (29.07 g, 147.5 mmol) in CH2Cl2 (150 ml) was added and the reaction mixture was stirred for 90 minutes and then allowed to warm to room temperature. Water (200 ml) was then added and the aqueous layer was reextracted with chloroform (3 times 100 ml). The organic layers were combined, washed with brine and dried (MgSO4). Evaporation of the solvent yielded crude product, which was distilled to give 12.96 g of the aldehyde: bp 90-5 (0.25 mm Hg); 1H NMR (CDCl3) δ1.05(d, 12H), 2.00- 2.67(m, 4H), 2.83-3.50(m, 4H), 9.67(s, 1H).

Provenance & Evidence