Dimethyl Sulfoxide → HCID 15382137, compound

Participants

Reaction Steps

A solution of oxalyl chloride (2.0 mL, 2.0M in CH2Cl2, 4.0 mmol) in 15 mL of CH2Cl2 was cooled to -78° C., and to it a solution of DMSO (0.5 mL, 7.8 mmol) in 1.0 mL of CH2Cl2 was added dropwise. The resulting solution was stirred for 3 min, at which time a solution of the alcohol 6 (0.88 g, 2.6 mmol) in 15 mL of CH2Cl2 was introduced via cannula. Stirring was continued at -78° C. for 15 min and then triethyl amine (1.8 mL, 13 mmol) was added. The mixture was allowed to warm to room temperature over a period of 10 min and was then poured into 50 mL of water. The layers were separated and the aqueous layer was extracted with 25 mL of CH2Cl2. Combined organic extracts were washed with water, brine and dried (MgSO4) and processed in the normal manner. The crude material was subjected to chromatography on silica gel to yield the aldehyde 7 (0.75 g, 88% yield) as a pale yellow liquid: Rf 0.4 (60% EtOAc/hexane); 1H-NMR (d6 -DMSO) δ9.58 (d, J=1.3 Hz, 1H), 4.85 (septet, J=6.2 Hz, 1H), 4.05 (m, 1H), 3.84 (broad m, 4H), 3.66 (s, 2H), 3.50 (m, 1H), 2.20 (m, 4H), 1.47 (m, 4H), 1.22 (broad m, 6H), 1.16 (d, J=7.2 Hz, 6H).

Provenance & Evidence