Ethyl Acetate → HCID 86594835, compound

HRID 2247439Notes

Reaction equation

HRID 2247439 reaction equation
C(O[C:5]1[CH:6]=[C:7]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([C:19]#[C:20][CH2:21]Br)[CH:12]=2)[CH:8]=[CH:9][CH:10]=1)(=O)C.[F:23][C:24]([F:33])([F:32])[C:25]1[CH:30]=[CH:29][C:28]([OH:31])=[CH:27][CH:26]=1.C(=O)([O-])[O-].[K+].[K+].[C:40]([O:43][CH2:44]C)(=[O:42])[CH3:41]>CN(C)C=O>[CH3:18][O:17][C:14]1[CH:15]=[CH:16][C:11]([C:7]2[CH:8]=[CH:9][CH:10]=[C:5]([CH2:41][C:40]([O:43][CH3:44])=[O:42])[CH:6]=2)=[CH:12][C:13]=1[C:19]#[C:20][CH2:21][O:31][C:28]1[CH:27]=[CH:26][C:25]([C:24]([F:32])([F:33])[F:23])=[CH:30][CH:29]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 678744-(Trifluoromethyl)phenolHCID 68634494HCID 68634494, compound

Product 1

HCID 86594835HCID 86594835, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6.8 mg of Methyl [3′-(3-bromo-1-propynyl)-4′-methoxybiphenyl-3-yl acetate was dissolved in 0.2 ml of N,N-dimethylformamide, 10 mg of 4-trifluoromethylphenol and 10 mg of potassium carbonate were added thereto, and the mixture was stirred at room temperature for 3 days. The reaction mixture was diluted with ethyl acetate and washed with water. The organic layer was concentrated to give methyl {4′-methoxy-3′-[3-(4-trifluoromethylphenoxy)-1-propynyl]biphenyl-3-yl}acetate. This product was dissolved in 0.4 ml of ethanol, then 0.1 ml of 5N aqueous sodium hydroxide was added thereto, and the mixture was stirred overnight at room temperature. 1N hydrochloric acid was added to the reaction mixture which was then extracted with ethyl acetate. The organic layer was concentrated, and the residue was purified by reverse-phase high performance liquid chromatography to give 4.89 mg of the title compound.

Workup

  1. washwashed with water
  2. concentrationThe organic layer was concentrated

Sources & evidence

ORD record
ord-a565d6e2c35547f598689544d88411b4
Source dataset
uspto-grants-2010_03
Patent number
US07687664B2

Reaction notes

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