Dimethyl Sulfoxide → HCID 71135270, compound

Participants

Reaction Conditions

Reaction Steps

Oxalyl chloride (0.09 mL of a 2M soln in DCM, 0.177 mmol) was dissolved in DCM (0.8 mL) at −78° C. DMSO (35 mg, 0.44 mmol) was added, and the resulting solution was stirred at −78° C. for 5 minutes. A solution of the product from step A (40 mg, 0.09 mmol) in DCM (1 mL) was added followed by Et3N (90 mg, 0.89 mmol). The reaction was warmed to room temperature, and stirred at that temperature for 15 minutes. The reaction was quenched with sat. NH4Cl(aq.), and extracted with DCM. The combined organic layers were dried (Na2SO4), filtered, and concentrated in vacuo. The residue was purified via silica gel column chromatography (0-15% EtOAc in hexanes) which provided title compound. 1H NMR (500 MHz, CDCl3) δ 6.94 (dd, 2H), 4.58 (d, 1H), 4.49 (d, 1H), 4.18-4.00 (br m, 2H), 3.58-3.46 (m, 2H), 2.74-2.61 (m, 2H), 1.83 (d, 1H), 1.73 (d, 1H), 1.47 (s, 9H), 1.38-1.19 (m, 5H), 1.13-1.09 (m, 2H), 0.97-0.88 (m, 1H), 0.80-0.68 (m, 2H), 0.06-0.00 (m, 1H). MS (ESI) m/z 450 [M+H]+.

Provenance & Evidence