Propyl mercaptan → 4-(Propylthio)butan-2-one

Solid sodium hydride (60% dispersion in oil, 2.90 g, 72.3 mmol) was added in portions over 5 minutes to a stirred solution of 1-propanethiol (6.00 g, 78.8 mmol) in tetrahydrofuran (262 mL). After 15 minutes, a thick white suspension had formed. To the suspension was added 1-chloro-3-butanone (7.00 g, 65.7 mmol), which caused the reaction mixture to warm and a cloudy solution to form. After 30 minutes, the cloudy solution was partitioned between ethyl acetate (100 mL) and water (100 mL). The layers were separated and the organic layer was washed with saturated aqueous sodium bicarbonate (100 mL) and brine (100 mL), dried over sodium sulfate, filtered, and concentrated under reduced pressure to afford a pale brown oil. The crude product was purified by flash chromatography (silica gel, elution with 20% ethyl acetate in hexanes) to provide 9.0 g of 4-(propylthio)butan-2-one as a clear liquid.

1. customa thick white suspension had formed
2. temperatureto warm
3. customa cloudy solution to form
4. waitAfter 30 minutes
5. customthe cloudy solution was partitioned between ethyl acetate (100 mL) and water (100 mL)
6. customThe layers were separated
7. washthe organic layer was washed with saturated aqueous sodium bicarbonate (100 mL) and brine (100 mL)
8. dry with materialdried over sodium sulfate
9. filtrationfiltered
10. concentrationconcentrated under reduced pressure
11. customto afford a pale brown oil
12. customThe crude product was purified by flash chromatography (silica gel, elution with 20% ethyl acetate in hexanes)

ORD record

ord-f7c6cf06c0284e6694eb3d72b9f21271

Source dataset

uspto-grants-2015_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09145410B2