HCID 68524438, compound → 3-(4-Iodophenyl)-4-cyano-5-ethyl-thiophene-2-carboxylic acid ethyl ester

Participants

Reaction Conditions

Reaction Steps

Add dropwise diethylzinc (1.0M in hexanes, 7 ml, 6.99 mmol, 3 eq) to a mechanically stirring suspension of 4-cyano-3-(4-iodo-phenyl)-5-methylsulfanyl-thiophene-2-carboxylic acid ethyl ester (1 gr, 2.33 mmol) and 1,3-bis-(diphenylphosphino)propane nickel (II) chloride (24 mg, 0.0466 mmol, 0.02 eq) in dry THF (12 ml) and heat the resulting mixture 60° C. for 30 min. Cool the reaction to room temperature and remove solvents in vacuo. Purify the solid by chromatography on silica gel (eluting with 10-80% Ethyl acetate/hexane) to provide the title compound in 60% yield: Mass spectrum (EI+): m/z 412 (M++1); 1H NMR (CDCl3, 200 MHz): δ 7.72 (d, 2H, J=8.5); 7.05 (d, 2H, J=8.5); 4.14 (q, 2H, J=7.2); 3.01 (q, 2H, J=7.2); 1.36 (t, 3H, J=7.5); 1.17 (t, 3H, J=7.2).

Provenance & Evidence