5-(2,3-Difluorophenyl)nona-1,8-dien-5-ol → (Z)-1-(2,3-difluorophenyl)cyclohept-4-enol

Participants

Reaction Conditions

Reaction Steps

In a 500 mL round-bottomed flask (t=g) was added 5-(2,3-difluorophenyl)nona-1,8-dien-5-ol (1.15 g, 4.56 mmol) in CH2Cl2 (50 mL) to give a colorless solution. Grubbs II (0.193 g, 0.228 mmol) was added, and the mixture was heated at 45° C. for 19 hours. TLC showed clean conversion to a more polar spot. Combined material with 68908-184 and concentrated to dryness and the residue was subject to purification up to 50% Et2O/hexane. The major peak was pooled and concentrated to a colorless oil (0.761 g, 74.5%). 1H NMR showed the majority as the desired product (same as the later synthesized compound using Grubbs I catalyst) and a minor component with double-bond isomerized.

Provenance & Evidence