Dimethylformamide → HCID 69202581, compound

Participants

Reaction Steps

(E)-3-(3,5-dimethoxy-phenyl)-acrylonitrile (0.4 g, 2.1 mmol), 4-iodo-1,2-(methylenedioxy)benzene (0.75 g, 3 mmol), Pd(OAc)2 (0.047 g, 0.21 mmol), KOAc (0.62 g, 6.3 mmol) and tetrabutylammonium bromide (0.75 g, 2.3 mmol) were placed in a microwave vial, DMF (3 mL) added and the reaction mixture degassed. The vial was placed in the microwave oven (Emrys Optimizer) at 150° C. for 1 hour. The contents were poured into a water-EtOAc mixture (40 mL, 1:1) and filtered through Celite® washing the filtrate with EtOAc. The organic layer was separated and the crude product isolated by CC (silica gel, hexanes:EtOAc, 3:1 to 1:1). Sonication of the purified solid with an ether:hexane mixture yields (E) 3-benzo[1,3]dioxol-5-yl-3-(3,5-dimethoxy-phenyl) -acrylonitrile (0.2 g, 0.65 mmol) in 31% yield: m.p 95-96° C.; 1H NMR (CDCl3) δ 6.85-6.82 (m, 1H, Ar), 6.79-6.78 (m, 2H, Ar), 6.55-6.52 (m, 3H, Ar), 6.01(s, 2H, CH2), 5.63(s, 1H, CH), 3.8 (s, 6H, 2CH3). Anal. Calcd. for C18H15NO4: C, 69.89; H, 4.89; N, 4.53. Found: C, 69.69; H, 5.12; N, 4.46.

Provenance & Evidence