Methyl 2',5'-difluoro-4-(hydroxymethyl)-1,1'-biphenyl-2-carboxylate → 1-(2',5'-Difluoro-4-(hydroxymethyl)-1,1'-biphenyl-2-yl)-2,2-dimethyl-1-propanone

HRID 1662548Notes

Reaction equation

HRID 1662548 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C:9]1[C:10]([C:17]([O:19]C)=O)=[CH:11][C:12]([CH2:15][OH:16])=[CH:13][CH:14]=1.[C:21]([Li])([CH3:24])([CH3:23])[CH3:22]>C1COCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][C:12]([CH2:15][OH:16])=[CH:11][C:10]=1[C:17](=[O:19])[C:21]([CH3:24])([CH3:23])[CH3:22]

Participants

4

Reactant 2

HCID 57705744Methyl 2',5'-difluoro-4-(hydroxymethyl)-1,1'-biphenyl-2-carboxylateHCID 178418306HCID 178418306, compound

Product 1

HCID 577061821-(2',5'-Difluoro-4-(hydroxymethyl)-1,1'-biphenyl-2-yl)-2,2-dimethyl-1-propanoneYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 83.27C (0.485 g, 2 mmol) in THF (17 mL) at −78° C. was added tert butyl lithium (3 mL, 5 mmol, 1.7 M). The reaction was then stirred for 1.5 hours and then quenched with a saturated solution of ammonium chloride and 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 then purified on silica gel (0-40% EtOAc in hexanes) to yield 83.27D as a colorless oil (0.450 g, 85% yield).

Workup

  1. customquenched with a saturated solution of ammonium chloride
  2. extractionextracted three times with EtOAc
  3. dry with materialAfter drying over anhydrous magnesium sulfate
  4. filtrationfiltering
  5. customthe organic solvent was removed under reduced pressure
  6. customthe product was then purified on silica gel (0-40% EtOAc in hexanes)

Sources & evidence

ORD record
ord-339a2c087c7e44e988ce056b5c564250
Source dataset
uspto-grants-2011_10
Patent number
US08030354B2

Reaction notes

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