2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → Ethyl 4-cyano-3-(4-methoxyphenyl)-5-morpholin-4-ylthiophene-2-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a solution of ethyl 4-cyano-3-(4-methoxyphenyl)-5-morpholin-4-yl-2,3-dihydrothiophene-2-carboxylate (0.168 g, 0.45 mmol) in toluene (5 mL) was added 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (0.102 g, 0.45 mmol). The mixture was allowed to stir at 90° C. for 90 min and allowed to cool before filtration through Celite, eluting with toluene. The filtrate was concentrated and the residue was purified by column chromatography. The resulting orange solid was recrystallized from ethyl acetate/40-60 petroleum ether to give ethyl 4-cyano-3-(4-methoxyphenyl)-5-morpholin-4-ylthiophene-2-carboxylate (0.11 g, 66%). LCMS: (FA) ES+ 373. 1H NMR (400 MHz, d6-DMSO) δ: 7.28-7.31 (m, 2H), 6.96-7.00 (m, 2H), 4.06 (q, 2H), 3.81 (s, 3H), 3.76-3.79 (m, 4H), 3.59-3.61 (m, 4H) and 1.08 (t, 3H).

Provenance & Evidence