Dimethyl Sulfoxide → HCID 21904386, compound

Participants

Reaction Steps

To a solution of oxalyl chloride (0.22 ml, 2.54 mmol) in CH2Cl2 (2 ml) at −55° C. was added a solution of DMSO (0.30 ml, 4.24 mmol) in CH2Cl2 (1 ml). The mixture was stirred for 2 min. Then, a solution of 173 (230 mg, 1.06 mmol) in CH2Cl2 (1 ml) was added dropwise. After stirring for 15 min at −55° C., Et3N (1.4 ml) was added slowly. The mixture was stirred for 5 min and then warmed to room temperature. Aqueous NaHCO3 (5 ml) was added. The two layers were separated; and the aqueous layer was extracted with CH2Cl2 (2×5 ml). The combined organics were dried (Na2SO4), filtered and evaporated to give the crude product. Chromatography (1% MeOH in CH2Cl2) gave 174 as a light red liquid. 1H-NMR (300 MHz, CDCl3) (partial) δ 9.42 (s, 1H), 7.30 (m, 5H); LRMS (calculated for C14H17NO) 215, found 215.

Provenance & Evidence