1,2-Epoxybutane → HCID 69882854, compound

Participants

Reaction Steps

Sodium methoxide (0.075 g) was added to a stirred solution of (R)-N-[2,3-dichloro-4-mercaptophenyl]-2-hydroxy-2-methyl-3,3,3-trifluoropropanamide (Method 35) (0.44 g) in anhydrous THF (10 ml). The reaction mixture was stirred at ambient temperature for 5 minutes and 1,2-epoxybutane (0.11 ml) was added. The mixture was heated under reflux for 2 hours and allowed to cool to ambient temperature. EtOAc (150 ml) was added and the mixture washed with brine (100 ml) and dried. Volatile material was removed by evaporation and the residue was purified on a 20 g silica Mega Bond Elut column eluting with 1-40% EtOAc/isohexane to give the title compound (0.259 g) as an orange solid. NMR: 0.88 (t, 3H), 1.35-1.49 (m, 1H), 1.58 (s, 3H), 2.97-3.08 (m, 1H), 3.53-3.62 (m, 1H), 5.00 (d, 1H), 7.42 (d, 1H), 7.77 (d, 1H), 9.79 (brs, 1H); m/z: 404.

Provenance & Evidence