Dimethylformamide → HCID 69203598, compound

Participants

Reaction Steps

3-Benzo[1,3]dioxol-5-yl-acrylonitrile (9:1 (E):(Z) mixture) (0.3 g, 1.73 mmol), 4-iodo-anisole (0.57 g, 2.43 mmol), Pd(OAc)2 (0.039 g, 0.17 mmol), KOAc (0.5 g, 5.2 mmol) and tetrabutylammonium bromide (0.6 g, 1.9 mmol) were combined in a microwave vial and DMF (3 mL) added, the reaction mixture was then degassed. The reaction vessel was placed in the microwave oven (Emrys Optimizer) at 150° C. for 1 hour. The contents were poured into water, EtOAc mixture (40 mL, 1:1) and filtered through Celite washing with more 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 compound with an ether:hexane mixture yielded (Z) 3-benzo[1,3]dioxol-5-yl-3-(4-methoxy-phenyl)-acrylonitrile (0.16 g, 0.56 mmol) in 32% yield: m.p 80-81° C.; 1H NMR (CDCl3) δ 7.25(d, 2H, Ar), 6.98(dd, 1H, Ar), 6.89-6.86(m, 4H, Ar), 6.03(s, 2H, CH2), 5.56(s, 1H, CH), 3.84 (s, 3H, OCH3); Anal. Calcd for C17H13NO3: C, 73.11; H, 4.69; N, 5.02 Found: C, 73.02; H, 4.90; N, 4.82.

Provenance & Evidence