Triethylsilane → methyl 4-(2,4,6-trifluorobenzyl)-1H-pyrrole-2-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a TFA 30 mL solution of methyl 4-(2,4,6-trifluorobenzoyl)-1H-pyrrole-2-carboxylate in a sealed tube was added triethylsilane (2.55 g, 22 mmol). The resulting reaction mixture was heated in an oil bath at 70° C. overnight. The reaction was concentrated and diluted with isopropylacetate and saturated sodium bicarbonate aqueous solution. The organic layer was separated. The aqueous layer was extracted with isopropylacetate twice. The combined organic layers were dried over anhydrous sodium sulfate, filtered, concentrated and chromatographed on silica gel eluting with a gradient solvent mixture of AcOEt and hexanes to give the title compound (840 mg).

Provenance & Evidence