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

HRID 1099154Notes

Reaction equation

[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9]([OH:18])([CH2:14][CH2:15][CH:16]=[CH2:17])[CH2:10][CH2:11]C=C>C(Cl)Cl.Cl[Ru](=CC1C=CC=CC=1)([P](C1CCCCC1)(C1CCCCC1)C1CCCCC1)([P](C1CCCCC1)(C1CCCCC1)C1CCCCC1)Cl>[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9]1([OH:18])[CH2:10][CH2:11][CH:17]=[CH:16][CH2:15][CH2:14]1

Participants

Conditions

Temperature: 40 °C

Procedure

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).

Workup

customto give a colorless solution
concentrationconcentrated to dryness
customthe residue was subject to purification up to 50% Et2O/hexane (twice)
concentrationconcentrated to a light green oil (1.40 g, 89.2%)

Sources & evidence

ORD record: ord-e556eeeb277041419aece547ca7dac57
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08143403B2

Reaction notes

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