Methyl iodide → Methyl alpha-methylthio-alpha-[m-(2phenyl-1,3-dioxa-2-cyclopentyl)phenyl]propionate

温度

15 °C

Methyl α-methylthio[m-(2-phenyl-1,3-dioxa-2-cyclopentyl)phenyl]acetate (6.88 g) was dissolved in 30 ml of anhydrous dimethyl sulfoxide. While cooling at 15° C., 810 mg (65% content) of sodium hydride was added, and the mixture was stirred for 1 hour. Hydrogen evolved gradually to form a reddish brown solution. While cooling at 15° C., 1.5 ml of methyl iodide was added to this solution, whereupon the color vanished immediately. After stirring for 5 minutes, an aqueous solution of ammonium chloride (2 g/10 ml) was added, and then 40 ml of water was added. The mixture was extracted first with 50 ml of diethyl ether, and then three times with 10 ml of diethyl ether. The extract was washed three times with 10 ml of water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was chromatographed on a column of Florisil using benzene and diethyl ether as eluents to afford 6.14 g of methyl α-methylthio-α-[m-(2-phenyl-1,3-dioxa-2-cyclopentyl)phenyl]propionate as a colorless oil in a yield of 86%.

1. customto form a reddish brown solution
2. temperatureWhile cooling at 15° C.
3. stirringAfter stirring for 5 minutes
4. extractionThe mixture was extracted first with 50 ml of diethyl ether
5. washThe extract was washed three times with 10 ml of water
6. dry with materialdried over anhydrous sodium sulfate
7. concentrationconcentrated under reduced pressure
8. customThe residue was chromatographed on a column of Florisil

ORDレコード

ord-3363647c5a0f4b10b9c5eca6f643e91d

出典データセット

uspto-grants-1981_07

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US04278802