Methyl iodide → HCID 12917669, compound

Methyl α-methylthio(2-thienyl)acetate (1.980 g) was dissolved in 20 ml of anhydrous dimethylformamide, and with stirring at room temperature, 400 mg (65% content) of sodium hydride was added, whereupon hydrogen evolved vigorously. Ten minutes later, the reaction solution was cooled with ice, and 0.75 ml of methyl iodide was added over the course of 1 minute. The mixture was stirred at room temperature for 1 hour. An aqueous solution of ammonium chloride (0.50 g/30 ml) was added, and the mixture was extracted four times with 20 ml of diethyl ether. The organic layer was washed four times with 10 ml of water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was chromatographed on a silica gel column using benzene as an eluent to afford 1.949 g of methyl α-methylthio-α-(2-thienyl)propionate in a yield of 92%.

1. additionwas added over the course of 1 minute
2. stirringThe mixture was stirred at room temperature for 1 hour
3. extractionthe mixture was extracted four times with 20 ml of diethyl ether
4. washThe organic layer was washed four times with 10 ml of water
5. dry with materialdried over anhydrous sodium sulfate
6. concentrationconcentrated under reduced pressure
7. customThe residue was chromatographed on a silica gel column

ORD record

ord-e3c13cd75b9f40eca5e947d7b7733202

Source dataset

uspto-grants-1980_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04242519