Trifluoroacetic acid → 5-(2,3-Difluorophenyl)cyclohept-1-ene

Participants

Reaction Steps

In a 100 mL round-bottomed flask (t=g) was added (Z)-1-(2,3-difluorophenyl)cyclohept-4-enol (872 mg, 3.89 mmol) in CH2Cl2 (16 mL) to give a colorless solution. Triethylsilane (3.11 mL, 19.44 mmol) was added, following by TFA (8.00 mL). The mixture was stirred at room temperature for 2.5 hours. TLC showed clean conversion to a less polar compound. It was concentrated down and purification by FCC up to 20% Et2O in hexane afforded the desired product as a colorless oil (769 mg, 95%). The product was quickly eluted out. 1H NMR (the major peaks are the same as these in the later synthesis) confirmed the structure.

Provenance & Evidence