2-Propenoic acid, 2-cyano-3-methoxy-, ethyl ester, (2Z)- synthesis

Yield:42466-68-2 85%

Reaction Conditions:

with acetic anhydride;toluene-4-sulfonic acid at 85 - 90; for 20 h;Inert atmosphere;

Steps:

Ethyl (Z)-2-cyano-3-methoxyacrylate (6)

To a stirred solution of ethyl cyanoacetate (25 g, 0.22 mol) in trimethylorthoformate (36.5 mL, 0.33 mol), acetic anhydride (16 mL, 0.18 mol) and p-toluene sulfonic acid (0.5 g, 0.02 w/w) were added. The resultant solution was heated to 85-90 °C and stirred for 20 h. After reaction completion, the reaction mass was concentrated completely and the crude product was purified by methyl t-butyl ether slurry to obtain the desired product compound 6 as: Brown solid; yield 85%; 1H NMR (400 MHz, CDCl3): δ 1.32-1.36 (t, 3H, J1 = 7.2 Hz, J2 = 5.4 Hz), 4.12 (s, 3H), 4.30 (q, 2H, J = 9.6 Hz), 7.94 (s, 1H); LCMS (ESI) m/z for C7H9NO3: 156.2 Da ([M + H]+). Anal. calcd for C7H9NO3: C, 54.19; H, 5.85; N, 9.03; found: C,54.14; H, 5.89; N, 9.01%.

References:

Selvakumar, Balaraman;Vaidyanathan, Saraswathy P.;Madhuri, Subbiah;Elango, Kuppanagounder P. [Journal of Chemical Research,2017,vol. 41,# 4,p. 221 - 224]