Methyl iodide → Methyl alpha-methylthio-alpha-(m-(alpha,alpha-dimethoxybenzyl)phenyl)propionate

Methyl α-methylthio-[m-(α,α-dimethoxybenzyl)phenyl]acetate (444 mg) was dissolved in 4 ml of dimethyl sulfoxide, and 55 mg of sodium hydride (65% content) was added. The mixture was stirred at room temperature for 20 minutes. Methyl iodide (0.20 ml) was added dropwise over the course of 3 minutes, and the mixture was further stirred at room temperature for 30 minutes. An aqueous solution of ammonium chloride (200 mg/30 ml) was added, and the mixture was extracted three times with 20 ml of diethyl ether. The organic layer was washed three times with 10 ml of water, dried over anhydrous sodium sulfate, and the residue was chromatographed on a column of Florisil using benzene and methylene chloride as eluents to afford 386 mg of methyl α-methylthio-α-[m-(α,α-dimethoxybenzyl)phenyl]propionate as an oil in a yield of 84%.

1. stirringthe mixture was further stirred at room temperature for 30 minutes
2. extractionthe mixture was extracted three times with 20 ml of diethyl ether
3. washThe organic layer was washed three times with 10 ml of water
4. dry with materialdried over anhydrous sodium sulfate
5. customthe residue was chromatographed on a column of Florisil

ORD record

ord-ae7e6d9911ea4b70a56e79a245c8d30e

Source dataset

uspto-grants-1981_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04278802