Methyl iodide → HCID 18521403, compound

Participants

Reaction Steps

The resulting ethyl 2-methoxy-4-methylphenylacetate was dissolved in tetrahydrofuran (50 ml), and to the solution was added dropwise a 1.0 M solution of sodium bis(trimethylsilyl)amide in tetrahydrofuran (19 ml) at −70° C., the mixture was stirred at the same temperature for 1 hour, then methyl iodide (3.1 ml) was added dropwise to the mixture, and the mixture was further stirred at −30° C. for 1 hour. The reaction mixture was quenched with 2 M aqueous hydrochloric acid (15 ml), and extracted with ethyl acetate, and the organic layer was washed with water and saturated brine, and then dried over sodium sulfate. The solvent was evaporated under reduced pressure, and then the residue was purified by silica gel column chromatography (hexane/ethyl acetate=7/1) to give methyl 2-(2-methoxy-4-methylphenyl)propionate (2.65 g).

Provenance & Evidence