Tosylmethyl isocyanide → Methyl 4-methyl-1H-pyrrole-3-carboxylate

Participants

Reaction Steps

To a solution (100 mL) of potassium t-butoxide (23.0 g) in tetrahydrofuran was added dropwise a solution (50 mL) of p-toluenesulfonylmethyl isocyanide (25.0 g) and methyl crotonate (12.3 mL) in tetrahydrofuran with stirring under ice-cooling. After the completion of the dropwise addition, the ice bath was removed, and the reaction mixture was stirred at room temperature for 1 hr. The reaction mixture was filtered through celite, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel chromatography (ethyl acetate:hexane=1:4, volume ratio) to give the title compound (7.6 g, 42%) as an oil.

Provenance & Evidence