D-Psicose → Ethyl 3-(3-(4-cyano-2-methylphenyl)-4-(4-methoxyphenyl)thiophen-2-yl)propanoate

Participants

Reaction Steps

To a solution of (E)-ethyl 3-(3-(4-cyano-2-methylphenyl)-4-(4-methoxyphenyl)thiophen-2-yl)acrylate (Scheme I, 5A, X1=4-methoxyphenyl, X2=4-cyano-2-methylphenyl) (0.27 g, 0.669 mmol) in ethanol (40 mL) was added 10% Pd/C (0.25 g), and the reaction mixture was stirred at 20° C. under 20 Psi of hydrogen for 30 h. The reaction mixture was filtrated, and concentrated to give ethyl 3-(3-(4-cyano-2-methylphenyl)-4-(4-methoxyphenyl)thiophen-2-yl)propanoate (Scheme I, 6A, X1=4-methoxyphenyl, X2=4-cyano-2-methylphenyl) (0.2 g, yield 73.7%). 1H NMR (DMSO-d6 300 MHz): δ 7.71 (m, 2H), 7.45-7.40 (m, 2H), 6.92 (m, 2H), 6.75 (m, 2H), 4.03-3.96 (m, 2H), 3.66 (s, 3H), 2.76-2.71 (m, 3H), 1.80 (s, 2H), 1.22 (s, 1H), 1.14-1.09 (m, 3H).

Provenance & Evidence