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 1 L round-bottomed flask (t=g) was added 5-(2,3-difluorophenyl)nona-1,8-dien-5-ol (1.76 g, 6.98 mmol) in CH2Cl2 (600 mL) to give a colorless solution. Grubbs I (0.175 g, 0.209 mmol) was added, and the mixture was heated at 40° C. for 2 hours. TLC showed clean conversion to a more polar spot (some impurities from starting material remained). Combined with 68908-198 and concentrated to dryness and the residue was subject to purification up to 50% Et2O/hexane (twice). The major peak was pooled and concentrated to a light green oil (1.40 g, 89.2%). 1H NMR (400 MHz, CDCl3) δ 7.34-7.25 (m, 1H), 7.08-7.00 (m, 2H), 5.90-5.80 (m, 2H), 2.60-2.48 (m, 2H), 2.21 (t, J=7.0 Hz, 2H), 2.10-1.98 (m, 2H), 1.90-1.75 (m, 2H).

Provenance & Evidence