Acetone → HCID 16126089, compound

Participants

Reaction Steps

To a solution of 2-bromo-4-(1-methyl-propenyl)-thiophene (19.1 mmol, 4.15 g) in a cosolvent of acetone and water (15 mL/30 mL) was added at room temperature N-methyl morpholine oxide (NMO) (21.0 mmol, 4.92 g, 50% in H2O) and OsO4 (0.2 mmol, 1.27 g, 4% in H2O). The reaction mixture was stirred for 24 h at the temperature. After evaporation of acetone in vacuo, it was extracted with EtOAc (70 mL×4). The combined solution was washed with brine (70 mL), dried (MgSO4) and concentrated in vacuo. Chromatography on SiO2 (EtOAc/Hexanes, 2/3) gave 4.3 g (90%) of 2-(5-bromo-thiophen-3-yl)-butane-2,3-diol as an oil of isomeric mixture (major/minor, 8/1). Major isomer; 1H NMR (400 MHz, CDCl3) δ 7.10 (d, J=1.7 Hz, 1H), 7.02 (d, J=1.7 Hz, 1H), 3.81 (m, 1H), 2.54 (s, 1OH), 1.99 (d, J=5.7 Hz, 1OH), 1.53 (s, 3H), 1.04 (d, J=6.4 Hz, 3H). Minor isomer; 1H NMR (400 MHz, CDCl3) δ 7.14 (d, J=1.7 Hz, 1H), 7.04 (d, J=1.7 Hz, 1H), 3.90 (m, 1H), 2.58 (s, 1OH), 2.07 (d, J=4.0 Hz, 1OH), 1.46 (s, 3H), 1.13 (d, J=6.4 Hz, 3H).

Provenance & Evidence