Diethyl (cyanomethyl)phosphonate → 3-(3,4-Dimethoxyphenyl)-3-pyridin-4-ylacrylonitrile

3-(3,4-Dimethoxyphenyl)-3-pyridin-4-ylacrylonitrile was prepared analogously to methyl 3,3-bis-(3',4'-dimethoxyphenyl)acrylate using 4-(3,4-dimethoxybenzoyl)pyridine (1 g, 4 mmol), diethylcyanomethylphosphonate (0.73 mL, 4.4 mmol) and lithium hexamethyldisilazide (3.4 mL, 4.4 mmol, 1.3M) with a reaction time of 24 hours at room temperature. The crude product was slurried in 10 mL of hexane. The mixture was filtered, the solid was washed with hexane, air dried and then dried in vacuo to afford 0.91 g (85%) of a mixture of the E and Z isomers as an off white solid: mp 116-125° C.; 1H NMR (CDCl3) δ 8.80-8.63 (m, 4 H), 7.40-7.20 (m, 4 H), 7.04-6.74 (m, 6 H), 5.81 (s, 1 H), 5.70 (s, 1 H), 3.94 (s, 3 H), 3.92 (s, 3 H), 3.87 (s, 3 H), 3.84 (s, 3 H); 13C NMR (CDCl3) δ 160.1, 157.0, 151.6, 151.1, 150.3, 149.2, 148.9, 146.7, 144.9, 129.6, 127.8, 123.7, 123.1, 122.7, 122.1, 117.4, 117.1, 112.3, 111.0, 110.5, 96.1, 94.8, 56.0, 56.0; Anal. Calcd for C16H14N2O2. Theoretical: C, 72.17; H, 5.30; N, 10.52. Found: C, 72.35; H, 5.43; N, 10.47.

1. customwith a reaction time of 24 hours
2. customat room temperature
3. filtrationThe mixture was filtered
4. washthe solid was washed with hexane, air
5. customdried
6. customdried in vacuo

ORD-Eintrag

ord-c54dc71747614118bec023d3b9e16856

Quelldatensatz

uspto-grants-2000_10

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06130226