Dimethyl Sulfoxide → HCID 16126090, compound

Participants

Reaction Steps

A solution of oxalyl chloride (19.12 mmol, 2.43 g) in anhydrous CH2C12 (100 mL) was cooled to −50° C. to −60° C. DMSO (39.83 mmol, 2.83 mL) is added dropwise at a rapid rate, with stirring. After 5 min, a solution of 2-(5-bromo-thiophen-3-yl)-butane-2,3-diol (15.93 mmol, 4.0 g) in anhydrous CH2Cl2 (25 mL) was added dropwise over 10 min, keeping the temperature at −50° C. to −60° C. After 15 min stirring, triethylamine (80 mmol, 11.15 mL) was added dropwise, keeping the temperature below −50° C. Stirring was then continued for 5 min. The reaction mixture was allowed to warm to room temperature and water (100 mL) was added. The separated aqueous layer was extracted with CH2Cl2 (70 mL×2). The combined organic layer was washed with brine (100 mL), dried (MgSO4), concentrated in vacuo. Chromatography on SiO2 (EtOAc/Hexanes, 1/2) gave 3.2 g (81%) of 3-(5-bromo-thiophen-3-yl)-3-hydroxy-butan-2-one as an oil; 1H NMR (400 MHz, CDCl3) δ 7.22 (d, J=1.7 Hz, 1H), 6.98 (d, J=1.7 Hz, 1H), 4.48)s, 1OH), 2.16 (s, 3H), 1.72 (s, 3H).

Provenance & Evidence