Sodium Hydroxide → (2-(1,2-Dimethylpropyl)-2'-fluoro-5'-(methyloxy)-1,1'-biphenyl-4-yl)methanol

HRID 1662486Notes

Reaction equation

HRID 1662486 reaction equation
[CH3:1][CH:2]([C:6]1[CH:11]=[C:10]([C:12](OC)=[O:13])[CH:9]=[CH:8][C:7]=1[C:16]1[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[CH:18][C:17]=1[F:24])[CH:3]([CH3:5])[CH3:4].[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH-].[Na+]>C1COCC1>[CH3:1][CH:2]([C:6]1[CH:11]=[C:10]([CH2:12][OH:13])[CH:9]=[CH:8][C:7]=1[C:16]1[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[CH:18][C:17]=1[F:24])[CH:3]([CH3:4])[CH3:5]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 57705901Methyl 2-(1,2-dimethylpropyl)-2'-fluoro-5'-(methyloxy)-1,1'-biphenyl-4-carboxylate

Product 1

HCID 57705959(2-(1,2-Dimethylpropyl)-2'-fluoro-5'-(methyloxy)-1,1'-biphenyl-4-yl)methanolYield 24%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 69.12B (0.050 g, 0.2 mmol) in THF (3 mL) at 0° C. was added LAH (0.3 mL, 0.3 mmol, 1.0M). The reaction was stirred for one hour and then 1N NaOH(aq) was added to the mixture. The reaction was extracted three times with EtOAc. After drying over anhydrous magnesium sulfate and filtering, the organic solvent was removed under reduced pressure and the product was purified on silica gel (0-20% EtOAc in hexanes) to yield 69.12C as a colorless oil (0.011 g, 24% yield).

Workup

  1. extractionThe reaction was extracted three times with EtOAc
  2. dry with materialAfter drying over anhydrous magnesium sulfate
  3. filtrationfiltering
  4. customthe organic solvent was removed under reduced pressure
  5. customthe product was purified on silica gel (0-20% EtOAc in hexanes)

Sources & evidence

ORD record
ord-8debc30864a34e129fd9d376f983a2c3
Source dataset
uspto-grants-2011_10
Patent number
US08030354B2

Reaction notes

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