Trifluoroacetic acid → HCID 58238614, compound

Participants

Reaction Conditions

Reaction Steps

At 0° C. triethylsilane (0.89 g, 7.7 mmol, 1.3 equiv) was added to compound 2 (2.0 g, 5.9 mmol, 1.0 equiv) in dichloromethane (50 mL). Trifluoroacetic acid (3.36 g, 29.5 mmol, 5.0 equiv) was added dropwise while maintaining the temperature<5° C. The reaction was allowed to warm to room temperature at which point the solution became a yellowish-green color. The reaction was stirred for 18 hr, LC/MS and TLC indicated the reaction was complete. The reaction was carefully quenched with saturated sodium bicarbonate (100 mL). The layers were separated, the organic layer was dried over sodium sulfate and absorbed onto silica gel (5 g) by concentration under reduced pressure. This material was purified on a silica gel column (25 g) by eluting with heptanes (250 mL) and ethyl acetate (2%) in heptanes (250 mL). The desired product was isolated pure in nearly quantitative yield (1.9 g).

Provenance & Evidence