4-(4-(Benzyloxy)phenyl)-4-(2-fluorophenyl)cyclohex-2-enone → 4-(2-Fluorophenyl)-4-(4-hydroxyphenyl)cyclohexanone

HRID 2174433Notes

Reaction equation

HRID 2174433 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[F:28])[CH2:20][CH2:19][C:18](=[O:21])[CH:17]=[CH:16]2)=[CH:11][CH:10]=1)C1C=CC=CC=1.[H][H]>CCOC(C)=O.[Pd]>[F:28][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=1[C:15]1([C:12]2[CH:11]=[CH:10][C:9]([OH:8])=[CH:14][CH:13]=2)[CH2:16][CH2:17][C:18](=[O:21])[CH2:19][CH2:20]1

Participants

5

Reactant 2

HCID 712451374-(4-(Benzyloxy)phenyl)-4-(2-fluorophenyl)cyclohex-2-enoneHCID 178418361HCID 178418361, compound

Product 1

HCID 712451354-(2-Fluorophenyl)-4-(4-hydroxyphenyl)cyclohexanoneYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Compound 5 (300 mg, 8.05 mmol) was dissolved in EtOAc (15 mL). Pd/C (100 mg, 10%) was added. The flask was charged with hydrogen gas (vacuum, H2, vacuum, H2) and the mixture was stirred overnight at room temperature. The crude mixture was filtered through a pad of celite (eluated with 40 mL of EtOAc) and the solvent was evaporated under reduced pressure to yield 230 mg, 99% of 6. 1H-NMR (CDCl3) δ 7.37 (td, 1H, J=8.0 Hz and 1.7 Hz), 7.25-7.17 (m, 1H), 7.19 (d, 2H, J=8.7 Hz), 7.16-7.11 (m, 1H), 7.00-6.93 (m, 1H), 6.78 (d, 2H, J=8.2 Hz), 2.82-2.72 (m, 2H), 2.67-2.56 (m, 2H), 2.51-2.37 (m, 4H), 1.43 (s, H2O/OH); 13C-NMR (CDCl3) δ 211.9, 161.4 (d, J=248 Hz), 154.2, 136.7, 132.9 (d, J=10.8 Hz), 128.7 (d, J=8.8 Hz), 128.3 (d, J=5.0 Hz), 127.9 (d, 2C, J=1.1 Hz), 124.1 (d, J=3.5 Hz), 117.0 (d, J=24.2 Hz), 115.3 (2C), 44.2 (d, J=2.7 Hz), 38.5 (2C), 35.5 (d, 2C, J=4.6 Hz); 19F-NMR (CDCl3) δ−108.6 (m).

Workup

  1. filtrationThe crude mixture was filtered through a pad of celite (eluated with 40 mL of EtOAc)
  2. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-56436956d7b84737ba6d8eafeb1f6e7a
Source dataset
uspto-grants-2015_06
Patent number
US09061981B2

Reaction notes

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