Methanol → 3,5-Dioxohexanoic acid

Participants

Reaction Steps

N,O-Bis(trimethylsilyl)acetamide (BSA, 54.7 mL, 224 mmol) was added to a stirred suspension of uracil (10.2 g, 90.7 mmol) and Compound 54 (31.1 g, 60.4 mmoles) in dry acetonitrile (300 mL). After stirring at rt for 30 min a clear solution was observed, and the reaction was cooled to 0 OC under nitrogen. Trimethylsilyfluoromethanesulfonate (TMSOTf, 21.9 mL, 121 mmol) was added and after the reaction was stirred at rt for 15 min, it was transferred to a preheated oil bath at 80° C. After stirring for 4 h at 80° C., the reaction was cooled to rt and MeOH (20 mL), EtOAc (250 mL) and H2O (400 mL) were added. The organic phase was then sequentially washed with sat. NaHCO3, brine, dried (Na2SO4) and concentrated to provide the crude triacetate. TLC(Rf=0.60, 80% EtOAc/hexanes). LCMS (Method DRHI), m/z=567.1 (M+H).

Provenance & Evidence