Ethyl bromoacetate → Ethyl[4-(1,1-dimethyl-2{3-methyl-5-[4-(trifluoromethyl)phenyl]thien-2-yl}-2-oxoethyl)-2-methylphenoxy]acetate

HRID 9669

Reaction equation

HRID 9669 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:28])([CH3:27])[C:9]([C:11]2[S:12][C:13]([C:17]3[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=3)=[CH:14][C:15]=2[CH3:16])=[O:10])=[CH:4][C:3]=1[CH3:29].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:37][C:38]([O:40][CH2:41][CH3:42])=[O:39]>C(#N)C>[CH2:41]([O:40][C:38](=[O:39])[CH2:37][O:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:27])([CH3:28])[C:9]([C:11]2[S:12][C:13]([C:17]3[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:24])[F:25])=[CH:19][CH:18]=3)=[CH:14][C:15]=2[CH3:16])=[O:10])=[CH:4][C:3]=1[CH3:29])[CH3:42]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 10796Cesium carbonateHCID 219864612-(4-Hydroxy-3-methylphenyl)-2-methyl-1-{3-methyl-5-[4-(trifluoromethyl)phenyl]thien-2-yl}propan-1-one2×

Product 1

HCID 21986375Ethyl[4-(1,1-dimethyl-2{3-methyl-5-[4-(trifluoromethyl)phenyl]thien-2-yl}-2-oxoethyl)-2-methylphenoxy]acetate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 2-(4-hydroxy-3-methylphenyl)-2-methyl-1-{3-methyl-5-[4-(trifluoromethyl)phenyl]thien-2-yl}propan-1-one (intermediate 105, 62.0 mg) in anhydrous acetonitrile (2 ml) was added caesium carbonate (106 mg) and ethyl bromoacetate (18 μl) and the reaction stirred at room temperature under nitrogen for 20 hours. The solid residue was filtered, and the filtrate was concentrated in vacuo and the residue purified by flash column chromatography, eluting with 1% EtOAc/cyclohexane yielded the title compound as a white solid.

Workup

  1. filtrationThe solid residue was filtered
  2. concentrationthe filtrate was concentrated in vacuo
  3. customthe residue purified by flash column chromatography
  4. washeluting with 1% EtOAc/cyclohexane

Sources & evidence

ORD record
ord-0d961a5452df42c8855de61b7e83107b
Source dataset
uspto-grants-2006_08
Patent number
US07091237B2

Linked notes

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