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

HRID 1049612Notes

Reaction equation

HRID 1049612 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[CH:26](O)[CH2:27][CH2:28][C:29]([CH3:32])([CH3:31])[CH3:30]>CO.[C].[Pd]>[CH3:30][C:29]([CH3:32])([CH3:31])[CH2:28][CH2:27][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

4

Reactant 1

HCID 1177598701-(2'-Fluoro-5'-methoxy-4-((4-methoxybenzyl)oxy)-[1,1'-biphenyl]-2-yl)-4,4-dimethylpentan-1-ol

Product 1

HCID 1177600752-(4,4-Dimethylpentyl)-2'-fluoro-5'-methoxy-[1,1'-biphenyl]-4-olYield 92.9%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

A solution (8.7 mL) of 1-(2′-fluoro-5′-methoxy-4-((4-methoxybenzyl)oxy)-[1,1′-biphenyl]-2-yl)-4,4-dimethylpentan-1-ol (394 mg) and 10% palladium-carbon (168 mg) in methanol was stirred under a hydrogen balloon atmosphere at room temperature for 9 hr. The reaction mixture was filtered, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (256 mg) as a colorless oil.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe solvent was evaporated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-8c270eb123aa49f7a108c3f8af2b0054
Source dataset
uspto-grants-2016_07
Patent number
US09382188B2

Reaction notes

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