Sodium Carbonate → 1-[4'-(Trifluoromethyl)-4-biphenylyl]-1-pentanone

HRID 1391745Notes

Reaction equation

HRID 1391745 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:13])[CH2:9][CH2:10][CH2:11][CH3:12])=[CH:4][CH:3]=1.[F:14][C:15]([F:26])([F:25])[C:16]1[CH:21]=[CH:20]C(B(O)O)=[CH:18][CH:17]=1.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:14][C:15]([F:26])([F:25])[C:16]1[CH:21]=[CH:20][C:1]([C:2]2[CH:7]=[CH:6][C:5]([C:8](=[O:13])[CH2:9][CH2:10][CH2:11][CH3:12])=[CH:4][CH:3]=2)=[CH:18][CH:17]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 742844'-MethylvalerophenoneHCID 27343894-(Trifluoromethyl)phenylboronic acid

Product 1

HCID 586298951-[4'-(Trifluoromethyl)-4-biphenylyl]-1-pentanoneYield 66.9%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

To a solution of 1-(4-methylphenyl)-1-pentanone (1.00 g, 4.15 mmol) in DME (20 mL) and water (10 mL) was added 4-(trifluoromethyl)benzeneboronic acid (870 mg, 4.57 mmol) and Na2CO3 (1.10 g, 10.38 mmol). After 10 minutes under nitrogen, Pd(PPh3)4 (480 mg, 0.42 mmol) was added portion-wise, and the mixture heated to reflux and stirred under nitrogen for 2 hours. The reaction mixture was then allowed to cool to rt and the solvents removed under vacuum. The resulting residue was partitioned between water and EtOAc, the layers separated and the aqueous re-extracted with EtOAc (3×30 mL). The combined organic extract was separated and dried (MgSO4), and the solvent removed under vacuum. Purification by flash chromatography (silica), eluting with cyclohexane:EtOAc (19:1) afforded the title compound as a white solid (850 mg).

Workup

  1. temperaturethe mixture heated
  2. temperatureto reflux
  3. customthe solvents removed under vacuum
  4. customThe resulting residue was partitioned between water and EtOAc
  5. customthe layers separated
  6. extractionthe aqueous re-extracted with EtOAc (3×30 mL)
  7. extractionThe combined organic extract
  8. customwas separated
  9. dry with materialdried (MgSO4)
  10. customthe solvent removed under vacuum
  11. customPurification by flash chromatography (silica)
  12. washeluting with cyclohexane:EtOAc (19:1)

Sources & evidence

ORD record
ord-a7245b5c7d3948bea33dfd909639bbd6
Source dataset
uspto-grants-2008_03
Patent number
US07338960B2

Reaction notes

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