2'-Fluoro-2-(1-hydroxy-2,2-dimethyl-but-3-enyl)-5'-methoxy-biphenyl-4-carboxylic acid methyl ester → Methyl 2'-fluoro-2-(1-hydroxy-2,2-dimethylbutyl)-5'-(methyloxy)-1,1'-biphenyl-4-carboxylate

HRID 1662459Notes

Reaction equation

HRID 1662459 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]([C:16]([O:18][CH3:19])=[O:17])=[CH:12][C:11]=1[CH:20]([OH:26])[C:21]([CH3:25])([CH3:24])[CH:22]=[CH2:23]>CO.[Pd]>[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]([C:16]([O:18][CH3:19])=[O:17])=[CH:12][C:11]=1[CH:20]([OH:26])[C:21]([CH3:25])([CH3:24])[CH2:22][CH3:23]

Participants

4

Reactant 1

HCID 574676322'-Fluoro-2-(1-hydroxy-2,2-dimethyl-but-3-enyl)-5'-methoxy-biphenyl-4-carboxylic acid methyl ester

Product 1

HCID 57706901Methyl 2'-fluoro-2-(1-hydroxy-2,2-dimethylbutyl)-5'-(methyloxy)-1,1'-biphenyl-4-carboxylateYield 86.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 66.60D (0.453 g, 1.26 mmol) in MeOH (10 mL) (degassed by N2), was added palladium on carbon (0.135 g, 1.26 mmol). The resulting mixture was stirred at room temperature under H2 for 18 hrs. The reaction mixture was then filtered through silica gel. After removing solvent, 66.62A (394 mg) was obtained as a colorless oil.

Workup

  1. filtrationThe reaction mixture was then filtered through silica gel
  2. customAfter removing solvent

Sources & evidence

ORD record
ord-c278b60e77d04d789c80177872c9efbf
Source dataset
uspto-grants-2011_10
Patent number
US08030354B2

Reaction notes

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