Acetonitrile → HCID 86621470, compound

Participants

Reaction Steps

A stirred suspension of 1 (0.77 g, 2.24 mmol), TEA (1.86 mL, 13.4 mmol), t-butylacrylate (1.96 mL, 13.4 mmol), Pd(OAc)2 (0.12 g, 0.50 mmol), P(o-tolyl)3 (0.28 g, 0.90 mmol) and CH3CN were stirred at reflux under N2. Heating was discontinued after 2 h and the reaction diluted with EtOAc (50 mL) and water (50 mL). The mixture was filtered through a celite pad and the filtrate transferred to a separatory funnel. The organic fraction was washed with 50 mL brine (50 mL), dried (MgSO4), filtered and concentrated to 1.39 g of an amber oil. The crude product was purified by flash chromatography on silica gel with a hexanes to 5% EtOAc:hexanes gradient. The product, 2, was isolated as a colorless, viscous oil (900 mg, 100%). 1H NMR (300 MHz, DMSO-d6): δ 1.52 (s, 9H), 1.59 (s, 8H), 2.31 (br, 4H), 6.51 (d, J=16 Hz, 1H), 7.19-7.38 (m, 7H), 7.56 (d, J=16 Hz, 1H), 7.66 (d, J=8.1 Hz, 2H).

Provenance & Evidence