Methyl diethylphosphonoacetate → HCID 69203667, compound

Participants

Reaction Steps

(3,4-Dimethoxyphenyl)-(3,5-dimethoxyphenyl)methanone (1.50 g, 4.95 mmol), (diethoxyphosphoryl)acetic acid methyl ester (2.29 g, 9.90 mmol), and lithium bis(trimethylsilyl)amide (1.0 M solution in THF, 9.90 ml, 9.90 mmol) were treated in the same manner as described above for the synthesis of 3-(3,5-dimethoxy-phenyl)-3-(3-methoxy-phenyl)-acrylonitrile. The crude yellowish oil was purified via preparative HPLC to give 3-(3,4-dimethoxy-phenyl)-3-(3,5-dimethoxy-phenyl)-acrylic acid ethyl ester as a light yellow oil (0.79 g, 43%): 1HNMR (CDCl3) δ 6.89-6.72 (m, 2H, Ar), 6.48-6.45 (m, 4H, Ar), 6.28 (s, 1H, double bond proton), 4.09 (q, J=7 Hz, 2H, CH2CH3), 3.92 (s, 3H, OCH3), 3.82 (s, 3H, OCH3), 3.75 (s, 6H, 2OCH3), 1.16 (t, J=7 Hz, 3H, CH2CH3). The product was carried over to the next step.

Provenance & Evidence