Methyl iodide → HCID 18521403, compound

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).

1. stirringthe mixture was further stirred at −30° C. for 1 hour
2. customThe reaction mixture was quenched with 2 M aqueous hydrochloric acid (15 ml)
3. extractionextracted with ethyl acetate
4. washthe organic layer was washed with water and saturated brine
5. dry with materialdried over sodium sulfate
6. customThe solvent was evaporated under reduced pressure
7. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=7/1)

ORD record

ord-c939a3f572014a2eba689f624bbf63a2

Source dataset

uspto-grants-2012_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08148421B2