Methyl iodide → HCID 12819459, compound

Participants

Reaction Conditions

Reaction Steps

A solution of methyl 2-(thiophen-2-yl)acetate (4.90 g, 31.4 mmol) in THF (25 ml) was added dropwise to a suspension of sodium hydride (1.20 g, 31.4 mmol, 60%) in THF (25 ml) at −50° C. under an atmosphere of nitrogen. After the reaction mixture was stirred for 1 h, methyl iodide was added (1.76 ml, 28.2 mmol) as solution in THF (25 ml) slowly at −50° C. over a period of 15 min. The reaction mixture was warmed up to −30° C. and continued to stir for another 2 h. It was quenched with aqueous ammonium chloride, extracted with DCM (2×30 ml) and washed with brine (30 ml). The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated under vacuo. The crude was purified by column chromatography over silica gel (100-200 mesh) using ethyl acetate (5%) in petroleum ether as eluent to get 2.2 g (41.7%) of methyl 2-(thiophen-2-yl)propanoate as a colorless liquid.

Provenance & Evidence