Dimethyl Sulfoxide → HCID 19810541, compound

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Reaction Steps

A solution of oxalyl chloride (0.9 ml, 10 mmol in 25 ml of CH2Cl2) was slowly added to a flask containing DMSO (1.5 ml, 21 mmol in 3 ml CH2Cl2 at -60° C. under N2. After 5 min, the alcohol from Example 52 (3 g, 10 mmol, 5 ml CH2Cl2) was added dropwise over 5 min period. After stirring the contents for 30 min, Et3N (6.3 ml, 45 mmol) was added and the mixture was warmed to room temperature. The suspension was stirred for 1 h and then poured to a slurry of CH2Cl2 -H2O-ice. The organic layer was washed with dilute HCl, brine, dried over MgSO4, and finally concentrated in vacuo. The crude product was purified by column chromatography (silica gel, Hexane-AcOEt, 4:1) which gave 2.85 g (95%) of the title compound: 1H NMR (CDCl3, 300 MHz) δ: 9.70 (t,J=1Hz,1H,--CHO), 7.40-7.10 (m,10H), 5.05 (s,2H), 3.95 (t,J=6Hz,1H), 2.75 (m,2H), 2.41 (m,2H), and 1.90 (m,2H); DCI-NH3 -MS, m/z 314 (MNH4+, 100%), and 297 (MH+, 20%).

Provenance & Evidence