3-(3-Fluorophenyl)-7-hydroxychromen-4-one → 3-(3-Fluorophenyl)chroman-7-ol

HRID 31308Notes

Reaction equation

HRID 31308 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[C:17](=O)[C:16]3[C:11](=[CH:12][C:13]([OH:19])=[CH:14][CH:15]=3)[O:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1>C(O)C.[Pd]>[F:1][C:2]1[CH:3]=[C:4]([CH:8]2[CH2:17][C:16]3[C:11](=[CH:12][C:13]([OH:19])=[CH:14][CH:15]=3)[O:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 179785433-(3-Fluorophenyl)-7-hydroxychromen-4-one

Product 1

HCID 179784803-(3-Fluorophenyl)chroman-7-ol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

3-(3-Fluorophenyl)-7-hydroxychromen-4-one (160 mg) was dissolved in ethanol (40 ml) and 10% palladium on carbon (400 mg) was added. The reaction mixture was hydrogenated for 6 hours at normal pressure and room temperature. It was then filtered through Celite and washed with ethanol. The solvent was evaporated under reduced pressure to give 3-(3-fluorophenyl)chroman-7-ol. 1H NMR (400 MHz, d6-DMSO) δ: 9.19 (br s, 1H), 7.38 (m, 1H), 7.17-7.21 (m, 2H), 7.08 (m, 1H), 6.88 (d, 1H, J 8.2 Hz), 6.30 (dd, 1H, J 8.2, 2.4 Hz), 6.20 (d, 1H, J 2.4 Hz), 4.22 (dd, 1H, J 10.3, 3.6 Hz), 4.02 (t, 1H, 10.3 Hz), 3.20 (m, 1H), 2.90 (m, 2H).

Workup

  1. filtrationIt was then filtered through Celite
  2. washwashed with ethanol
  3. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-cc9e6509cbd344cfbaca3f92dfb0a01f
Source dataset
uspto-grants-2008_09
Patent number
US07425568B2

Reaction notes

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