Water → {4-[4-Butyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-phenyl}-acetic acid methyl ester

HRID 2103436Notes

Reaction equation

HRID 2103436 reaction equation
[CH2:1]([C:5]1[N:6]=[C:7]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=2)[S:8][C:9]=1[CH2:10]Cl)[CH2:2][CH2:3][CH3:4].C(=O)([O-])[O-].[Cs+].[Cs+].[OH:28][C:29]1[CH:34]=[CH:33][C:32]([CH2:35][C:36]([O:38][CH3:39])=[O:37])=[CH:31][CH:30]=1.O>CN(C=O)C>[CH3:39][O:38][C:36](=[O:37])[CH2:35][C:32]1[CH:33]=[CH:34][C:29]([O:28][CH2:10][C:9]2[S:8][C:7]([C:12]3[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=3)=[N:6][C:5]=2[CH2:1][CH2:2][CH2:3][CH3:4])=[CH:30][CH:31]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 518900Benzeneacetic acid, 4-hydroxy-, methyl esterHCID 230893954-Butyl-5-chloromethyl-2-(4-trifluoromethyl-phenyl)-thiazole

Product 1

HCID 57804319{4-[4-Butyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-phenyl}-acetic acid methyl esterYield 75.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-butyl-5-chloromethyl-2-(4-trifluoromethyl-phenyl)-thiazole (278 mg, 0.83 mmol) in anhydrous DMF (5 mL) add cesium carbonate (297 mg, 1.66 mmol) and methyl 4-hydroxyphenylacetate (200 mg, 1.20 mmol). Stir the resulting mixture overnight then pour into water and extract twice with ethyl acetate. Wash the combined extracts with water, dry over MgSO4, filter and concentrate under vacuum to give the title compound (290 mg) as a yellowish solid.

Workup

  1. extractionextract twice with ethyl acetate
  2. washWash the combined extracts with water
  3. dry with materialdry over MgSO4
  4. filtrationfilter
  5. concentrationconcentrate under vacuum

Sources & evidence

ORD record
ord-9d9b7f8c25074795b24e7adc8d2acead
Source dataset
uspto-grants-2009_08
Patent number
US07576109B2

Reaction notes

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