1,2-Dichloroethane → HCID 44139977, compound

Participants

Reaction Steps

To a solution of Example 7B (800 mg, 3.3 mmol) in 1,2-dichloroethane (25 mL) was added isobutyraldehyde (1.8 mL, 19.6 mmol), acetic acid (0.37 mL, 6.5 mmol) and magnesium sulfate (2.5 g). The solution was stirred at room temperature overnight, filtered, and the filtrate washed with 10% NaHCO3 (2×20 mL) and brine (1×20 mL) and the resulting solution dried (MgSO4), the drying agent filtered off and the solvent removed in vacuo to give a crude residue which was purified by column chromatography on silica gel (20% ethyl acetate/hexane) to give the title compound as a colorless solid (710 mg, 73%). 1H NMR (d6-DMSO) δ 7.94, 7.91 (d, 1H), 7.75-7.63 (m, 2H), 7.51-7.43 (m, 1H), 5.62, 5.56 (d, 1H), 5.17-5.04 (m, 1H), 4.89, 4.85 (d, 1H), 4.80, 4.74 (d, 1H), 3.48 (s, 3H), 2.76-2.66 (m, 1H), 2.64-2.53 (m, 1H), 2.44-2.30 (m, 1H), 1.22-1.08 (m, 6H); MS (ESI) m/z 300 (M+H+).

Provenance & Evidence