Dichloromethane → Ethyl 2-(2-(tosyloxy)ethoxy)acetate

A mixture of ethyl (2-hydroxyethoxy)acetate (0.50 g, 3.37 mmol), triethylamine (1.4 ml) and methylene chloride (8 ml) was stirred under ice-cooling. Then, p-toluenesulfonyl chloride (0.96 g, 5.06 mmol) was added in small portions and the resulting mixture was stirred under ice-cooling for another 3 hours. The reaction mixture was poured into water and extracted with ethyl acetate, and the extract solution was washed with a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the resulting residue was purified by a silica gel column chromatography (eluent: ethyl acetate:n-hexane=1:5) to obtain 0.56 g of ethyl [2-(toluene-4-sulfonyloxy)ethoxy]acetate as a colorless oil.

1. temperaturecooling
2. stirringthe resulting mixture was stirred under ice-
3. temperaturecooling for another 3 hours
4. extractionextracted with ethyl acetate
5. washthe extract solution was washed with a saturated aqueous sodium chloride solution
6. dry with materialdried over anhydrous magnesium sulfate
7. distillationThe solvent was distilled off under reduced pressure
8. customthe resulting residue was purified by a silica gel column chromatography (eluent: ethyl acetate:n-hexane=1:5)

ORD record

ord-1a6e9201960f468aa0640fbc954b1e57

Source dataset

uspto-grants-2001_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06271251B1