[4-fluoro-2-[(E)-2-(4-fluorophenyl)ethenyl]phenyl]methanol → [4-Fluoro-2-[2-(4-fluorophenyl)ethyl]phenyl]methanol

HRID 514494Notes

Reaction equation

HRID 514494 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][OH:9])=[C:4](/[CH:10]=[CH:11]/[C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)[CH:3]=1>[Pd].CO>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][OH:9])=[C:4]([CH2:10][CH2:11][C:12]2[CH:13]=[CH:14][C:15]([F:18])=[CH:16][CH:17]=2)[CH:3]=1

Participants

4

Reactant 1

HCID 86725608[4-fluoro-2-[(E)-2-(4-fluorophenyl)ethenyl]phenyl]methanol

Product 1

HCID 86725612[4-Fluoro-2-[2-(4-fluorophenyl)ethyl]phenyl]methanolYield 37%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Charged [4-fluoro-2-[(E)-2-(4-fluorophenyl)ethenyl]phenyl]methanol (568 mg, 2.31 mmol, EXAMPLE 119, part A), Pd/C (65 mg) and methanol (6 mL) to a flask, the mixture was then purged with hydrogen, stirred at room temperature overnight. It was then filtered, filtrate concentrated to give a residue which was purified by flash column chromatograph to give 214 mg of the title compound (37%). 1H NMR (400 MHz, CDCl3): δ 1.42 (1H, t, J=5.2 Hz), 2.83-2.98 (4H, m), 4.59 (2H, d, J=5.6 Hz), 6.88-6.98 (4H, m), 7.08-7.11 (2H, m), 7.29-7.33 (1H, m).

Workup

  1. customthe mixture was then purged with hydrogen
  2. filtrationIt was then filtered
  3. concentrationfiltrate concentrated
  4. customto give a residue which
  5. customwas purified by flash column chromatograph

Sources & evidence

ORD record
ord-c90c8e78c0e0458da53eaa0c7d728895
Source dataset
uspto-grants-2015_08
Patent number
US09107916B2

Reaction notes

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