Water → HCID 59729399, compound

HRID 1669339Notes

Reaction equation

HRID 1669339 reaction equation
CON(C)[C:4]([C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=2)=[C:8]([CH3:22])[CH:7]=1)=[O:5].[CH2:24]([Mg]Br)[CH2:25][CH2:26][CH2:27][CH2:28][CH3:29].O.[Cl-].[Na+]>O1CCCC1.C(OCC)(=O)C>[CH3:22][C:8]1[CH:7]=[C:6]([C:4](=[O:5])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH:11]=[CH:10][C:9]=1[C:12]1[CH:13]=[CH:14][C:15]([C:18]([F:20])([F:21])[F:19])=[CH:16][CH:17]=1

Participants

7

Reactant 4

HCID 962WaterHCID 5234Sodium ChlorideHCID 866203622-Methyl-4'-trifluoromethyl-biphenyl-4-carboxylic acid methoxy-methyl-amideHCID 178444609HCID 178444609, compound

Product 1

HCID 59729399HCID 59729399, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Dissolve 2-methyl-4′-trifluoromethyl-biphenyl-4-carboxylic acid methoxy-methyl-amide (0.58 g, 1.8 mmol) in tetrahydro-furan (10 mL). Add hexyl magnesium bromide (2.0M ethyl ether, 2.69 mL, 5.39 mmol) at 0° C. under inert atmosphere and stir 1.5 hours. Quench reaction with saturated solution of ammonium chloride, dilute with ethyl acetate. Wash organic phase with water then saturated sodium chloride solution. Dry organic fraction with Na2SO4, filter and concentrate under reduced pressure. Purify on silica gel chromatography (0-30% Ethyl acetate/hexanes gradient) to provide 0.518 g of title compound (83%).

Workup

  1. customQuench
  2. customreaction with saturated solution of ammonium chloride
  3. filtrationDry organic fraction with Na2SO4, filter
  4. concentrationconcentrate under reduced pressure
  5. customPurify on silica gel chromatography (0-30% Ethyl acetate/hexanes gradient)

Sources & evidence

ORD record
ord-cc800b26b6a7450a8146eaf9abcb7e48
Source dataset
uspto-grants-2011_08
Patent number
US07989457B2

Reaction notes

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