Dimethyl Sulfoxide → HCID 19036656, compound

Participants

Reaction Conditions

Reaction Steps

A solution of DMSO (9.36 g, 120 mmol) in 20 mL of CH2Cl2 was added dropwise over 10 minutes to a solution of oxalyl chloride (10.16 g, 80 mmol) in CH2Cl2 (80 mL) at -70° C. under an atmosphere of nitrogen. After stirring for 15 minutes at -70° C., a solution of the product of step B (7.56 g, 40.0 mmol) in CH2Cl2 (50 mL) was added dropwise over 10 minutes and the solution was stirred at -70° C. for 15 minutes. Neat triethylamine (24.2 g, 240 mmol) was added rapidly, the ice bath was removed and the mixture allowed to warm to ambient temperature over 30 minutes. The reaction mixture was diluted with CH2Cl2 (100 mL), washed successively with water, 1N NaHSO4 and brine, dried (MgSO4), filtered through a pad of silica gel and eluted with CH2C2. The solvent was evaporated under reduced pressure affording 7.23 g of title product (97%) as a thick oil of sufficient purity to be used in the next reaction. 1H-NMR (300 MHz, CDCl3) δ1.67 (m, 4H), 2.47 (m, 2H), 2.70 (m, 2H), 7.37 (d, J=8 HZ, 2H), 7.48 (d, J=8 Hz, 2H), 9.77 (s, 1H).

Provenance & Evidence