Acrylonitrile → 6-Trifluoromethoxy-2H-chromene-3-carbonitrile

Participants

Reaction Conditions

Reaction Steps

To a microwave tube was added 2-hydroxy-5-trifluoromethoxybenzaldehyde (1 g, 5.0 mmol), 2-propenenitrile (1.6 mL, 24.3 mmol) and triethylenediamine (136 mg, 1.2 mmol). The reaction was heated in the microwave at 130° C. for 1 hour. After cooling, the resulting solution was diluted with ether (100 mL) and washed with 1N NaOH (50 mL), 1N HCl (50 mL) and brine (50 mL), dried (MgSO4), filtered and concentrated. Flash chromatography (0 to 15% EtOAc in hexanes over 1 hour) gave the product (600 mg) as a solid. m/z=242.4 (M+1), r.t.=3.72 mins. 1H NMR (400 MHz; CDCl3) δ 7.14-7.12 (2H, m), 7.00 (1H, s), 6.89 (1H, d), 4.85 (2H, s).

Provenance & Evidence