Trifluoroacetic acid → HCID 58238609, compound

Participants

Reaction Conditions

Reaction Steps

At 0° C. triethylsilane (1.09 g, 9.4 mmol, 1.3 equiv) was added to compound 7 (2.0 g, 7.2 mmol, 1.0 equiv) in dichloromethane (50 mL). Trifluoroacetic acid (4.1 g, 36.1 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 96 hr, LC/MS and TLC indicated the reaction was incomplete. The reaction was then refluxed for an additional 18 hr, at this point 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 (30 g) by eluting with heptanes (150 mL), ethyl acetate (2%) in heptanes (200 mL) and ethyl acetate (5%) in heptanes (200 mL). The desired product was isolated pure in nearly 70% yield (1.3 g).

Provenance & Evidence