Dimethyl Sulfoxide → HCID 131722684, compound

Participants

Reaction Steps

After cooling 0.605 g (4.767 mmole) oxalyl chloride in 30 mL DCM in a dry ice acetone bath under nitrogen, 0.748 g (9.569 mmole) DMSO in 5 mL DCM was added over 5 minutes. After stirring for 15 minutes, a solution of the alcohol (1.587 g, 3.987 mmole) from Step C above in 30 mL DCM was added over 20 minutes. After an additional 20 minutes, a solution of 2.017 g (19.935 mmole) triethylamine in 5 mL DCM was added over 5 minutes. The cooling bath was allowed to warm up overnight. The reaction mixture was transferred into a separatory funnel with ether and was washed with 1 N NaOH, water, and saturated brine. The organic layer was dried over sodium sulfate and concentrated to give 1.63 g crude product. FC on silica gel (5˜40% ethyl acetate in hexanes) gave 1.257 g title compound as a colorless oil. Rf: 0.44 (20% ethyl acetate in hexanes). 1H NMR (500 MHz) δ 9.64 (d, J=2.1 Hz, 1H), 7.33˜7.41 (m, 5H), 7.24˜7.27 (m, 1H), 6.90˜6.98 (m, 3H), 5.21 (AB d, J=12.2 Hz, 1H), 5.18 (AB d, J=12.2 Hz, 1H), 3.54˜3.58 (m, 1H), 3.26˜3.29 (m, 1H), 3.14˜3.22 (m, 3H), 2.89˜2.93 (m, 1H), 2.68˜2.71 (m, 1H), 1.86˜1.93 (m, 1H), 1.39˜1.47 (m, 1H), 1.04˜1.15 (m, 1H), 0.99 (d, J=6.7 Hz, 3H), 0.91 (t, J=7.5 Hz, 3H). Some starting material was also recovered (0.298 g). Rf: 0.13 (20% ethyl acetate in hexanes).

Provenance & Evidence