1-(2'-Fluoro-5'-methoxy-4-((4-methoxybenzyl)oxy)-[1,1'-biphenyl]-2-yl)-2,2-dimethylpentan-1-one → 2-(2,2-Dimethylpentyl)-2'-fluoro-5'-methoxy-[1,1'-biphenyl]-4-ol

HRID 1049608Notes

Reaction equation

HRID 1049608 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10]1[CH:15]=[CH:14][C:13]([O:16]CC2C=CC(OC)=CC=2)=[CH:12][C:11]=1[C:26](=O)[C:27]([CH3:32])([CH3:31])[CH2:28][CH2:29][CH3:30]>C1COCC1.C(O)(=O)C.[OH-].[OH-].[Pd+2]>[CH3:31][C:27]([CH3:32])([CH2:28][CH2:29][CH3:30])[CH2:26][C:11]1[CH:12]=[C:13]([OH:16])[CH:14]=[CH:15][C:10]=1[C:3]1[CH:4]=[C:5]([O:8][CH3:9])[CH:6]=[CH:7][C:2]=1[F:1]

Participants

5

Reactant 1

HCID 1177599071-(2'-Fluoro-5'-methoxy-4-((4-methoxybenzyl)oxy)-[1,1'-biphenyl]-2-yl)-2,2-dimethylpentan-1-one

Product 1

HCID 1177601582-(2,2-Dimethylpentyl)-2'-fluoro-5'-methoxy-[1,1'-biphenyl]-4-ol

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

1-(2′-Fluoro-5′-methoxy-4-((4-methoxybenzyl)oxy)-[1,1′-biphenyl]-2-yl)-2,2-dimethylpentan-1-one (43.3 mg) was dissolved in a mixed solution of THF (10 mL) and acetic acid (2 mL), and the reaction was performed in H-Cube having a 20% palladium hydroxide/carbon cartridge (70 mm) at 60° C., 40 atm, flow rate 1 ml/min for 17 hr. The solvent was evaporated under reduced pressure to give the title, compound. This compound was used for the next step without purification.

Workup

  1. customat 60° C.
  2. customThe solvent was evaporated under reduced pressure
  3. customto give the title, compound
  4. customThis compound was used for the next step without purification

Sources & evidence

ORD record
ord-d92855856047472a90b5cc73f8fc8a7a
Source dataset
uspto-grants-2016_07
Patent number
US09382188B2

Reaction notes

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