Methyl iodide → Methyl 3-methoxy-2-phenyl-2-propenoate

Participants

Reaction Conditions

Reaction Steps

Combine hexane washed sodium hydride (24 g, 60% in oil, 580 mmol) and tetrahydrofuran (400mL). Cool to about 5° C. Simultaneously, add dropwise methyl phenylacetate (40 g, 270 mmol) and the methyl formate (35 g, 580 mmol). Add methanol (0.5 mL). Warm to ambient temperature. After 18 hours, pass nitrogen gas over the reaction mixture to remove the solvent to give a residue. Dissolve the residue in dimethylformamide (400 mL) and cool to about 5° C. Slowly add methyl iodide (76 g, 540 mmol). After the addition is complete, warm to ambient temperature. After 3 hours, pour the reaction mixture into water and extract 2 times with diethyl ether. Extract the combined organic layers 5 times with water and once with aqueous saturated sodium chloride solution. Dry the organic layer over MgSO4 and evaporate in vacuo to give the title compound.

Provenance & Evidence