Trifluoroacetamide → HCID 131734805, compound

Participants

Reaction Steps

To a 1-L round-bottom flask containing 2,2,2-trifluoroacetamide (17.43 g), magnesium oxide (12.1 g), and rhodium(II) acetate (0.99 g) in anhydrous dichloromethane (500 mL) was added tert-butyldimethyl(3-(methylsulfinyl)propoxy)silane (17.65 g) and (diacetoxyiodo)benzene (36.1 g). The resulting reaction mixture was stirred at room temperature for 24 hours and then filtered through a short pad of celite. The filtrate was concentrated, the brown oily residue was taken up in MeOH (˜500 mL), and potassium carbonate (51.7 g) was added. The reaction mixture was stirred at RT for 2 hours. The mixture was then filtered through a pad of celite, the pad was washed with MeOH, and the filtrate was concentrated. The resulting soft brown solid was treated with DCM-EtOAc (4:1), the mixture was stirred at room temperature for 1 hour, and it was filtered again through a pad composed of silica gel and celite. The pad was washed with DCM-EtOAc (2:1) first and then with neat EtOAc only. The filtrate was concentrated and the brown oily residue was subject to a column chromatography (EtOAc-Hex 1:2 to neat EtOAc). Concentration of the product eluting fractions gave the title compound as a light brown oil (12.3 g).

Provenance & Evidence