Ethanol → HCID 22063786, compound

Participants

Reaction Steps

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%).

Provenance & Evidence