Ammonium Chloride → 1-(2'-Fluoro-4-(hydroxymethyl)-1,1'-biphenyl-2-yl)-2,2-dimethyl-1-propanone

HRID 1662417Notes

Reaction equation

HRID 1662417 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9]([C:16]([O:18]C)=O)=[CH:10][C:11]([CH2:14][OH:15])=[CH:12][CH:13]=1.[C:20]([Li])([CH3:23])([CH3:22])[CH3:21].[Cl-].[NH4+]>C1COCC1>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][C:11]([CH2:14][OH:15])=[CH:10][C:9]=1[C:16](=[O:18])[C:20]([CH3:23])([CH3:22])[CH3:21]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 57705859Methyl 2'-fluoro-4-(hydroxymethyl)-1,1'-biphenyl-2-carboxylateHCID 178418306HCID 178418306, compound

Product 1

HCID 577068821-(2'-Fluoro-4-(hydroxymethyl)-1,1'-biphenyl-2-yl)-2,2-dimethyl-1-propanoneYield 78%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 66.32C (0.850 g, 3 mmol) in THF (33 mL) at −78° C. was added tert-butyllithium (6 mL, 10 mmol, 1.7M). The reaction was stirred for 5 hours and then a saturated solution of ammonium chloride was added and the mixture 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 then purified on silica gel (0-40% EtOAc in hexanes) to yield 66.32D as a colorless oil (0.670 g, 72% yield).

Workup

  1. extractionthe mixture 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 then purified on silica gel (0-40% EtOAc in hexanes)

Sources & evidence

ORD record
ord-1b8cc68862674530854071c3acf5bd99
Source dataset
uspto-grants-2011_10
Patent number
US08030354B2

Reaction notes

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