Ethanol → HCID 22063786, compound

Ethyl thiooxamate (4.94 g, 37.1 mmol) was dissolved in anhydrous ethanol (250 ml), added with 1-bromopinacolone (4.99 ml, 37.1 mmol), and refluxed by heating for 4 hours. The reaction mixture was concentrated, neutralized with saturated aqueous sodium hydrogencarbonate, and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, and then the solvent was evaporated under reduced pressure. The residue was dissolved in anhydrous ethanol (200 ml), added with sodium hydroboride (2.10 g, 55.6 mmol), and stirred at room temperature for 16 hours. The reaction solution was further added with sodium borohydride (500 mg, 13.2 mmol) and stirred at room temperature for 4 hours, and then the solvent was evaporated under reduced pressure. The residue was cooled to −78° C., and the resulting white solid was taken by filtration to obtain the title compound (2.77 g, 44%).

1. temperaturerefluxed
2. temperatureby heating for 4 hours
3. concentrationThe reaction mixture was concentrated
4. extractionextracted with ethyl acetate
5. dry with materialThe organic layer was dried over sodium sulfate
6. customthe solvent was evaporated under reduced pressure
7. dissolutionThe residue was dissolved in anhydrous ethanol (200 ml)
8. stirringstirred at room temperature for 4 hours
9. customthe solvent was evaporated under reduced pressure
10. temperatureThe residue was cooled to −78° C.
11. filtrationthe resulting white solid was taken by filtration

ORD record

ord-f9a9817e13ad4507822eae0573711f43

Source dataset

uspto-grants-2006_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07056917B2