Thionyl Chloride → 405219-36-5

Dimethylformamide (5 drops) was added over 1 minute to a stirred solution of 2-(cyclopentyl)ethylsulfonic acid sodium salt (1 5.5 g, 87.5 mmol) in thionyl chloride (60 ml) under a nitrogen atmosphere. The reaction mixture was stirred under reflux for 5 hours and was then cooled to room temperature and concentrated under vacuum. The residue was suspended in toluene (100 ml) and then concentrated under vacuum. The residue was dissolved in a mixture of ethyl acetate (150 ml) and water (150 ml) and the organic phase was separated. The aqueous phase was extracted with ethyl acetate (100 ml) and the combined organic extracts were washed with brine (3×100 ml), dried (magnesium sulfate) and evaporated to give the title compound as a brown oil (14.1 g), Rf 0.5 (pentane/ethyl acetate 95:5).

1. temperatureunder reflux for 5 hours
2. concentrationconcentrated under vacuum
3. concentrationconcentrated under vacuum
4. dissolutionThe residue was dissolved in a mixture of ethyl acetate (150 ml) and water (150 ml)
5. customthe organic phase was separated
6. extractionThe aqueous phase was extracted with ethyl acetate (100 ml)
7. washthe combined organic extracts were washed with brine (3×100 ml)
8. dry with materialdried (magnesium sulfate)
9. customevaporated

ORD record

ord-dc6ab3b7ef9c4b9d9c760a52f8914e1f

Source dataset

uspto-grants-2003_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06670362B2