Methyl Thioglycolate → methyl 6-benzyl-5-phenyl-6H-thieno[2,3-b]pyrrole-2-carboxylate

Participants

Reaction Conditions

Reaction Steps

A solution (1.1 M) of 1-benzyl-2-chloro-5-phenyl-1H-pyrrole-3-carbaldehyde in THF at 0° C. was treated with methyl thioglycolate (1.5 eq.) and a solution (2 M) of potassium tert-butoxide (2.5 eq.) in THF. The mixture was stirred at 0° C. for 2 h then at RT for 40 h. The reaction was quenched with water and pH was turned to neutral value by addition of aqueous ammonium chloride (saturated solution). The mixture was extracted with AcOEt and the combined organic phase was washed with brine and dried. Evaporation of the solvent gave a residue that was purified by flash chromatography on silica gel (1:30 acetone/toluene) to afford the title compound (38%) as a solid.

Provenance & Evidence