Cesium carbonate → Methyl 4-[2-methyl-4-(2-{4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl}ethyl)phenoxy]butanoate

HRID 460033Notes

Reaction equation

HRID 460033 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH2:8][CH2:9][C:10]2[S:14][C:13]([C:15]3[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][CH:16]=3)=[N:12][C:11]=2[CH3:25])[CH:5]=[CH:4][C:3]=1[OH:26].Br[CH2:28][CH2:29][CH2:30][C:31]([O:33][CH3:34])=[O:32].C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C>[CH3:1][C:2]1[CH:7]=[C:6]([CH2:8][CH2:9][C:10]2[S:14][C:13]([C:15]3[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][CH:16]=3)=[N:12][C:11]=2[CH3:25])[CH:5]=[CH:4][C:3]=1[O:26][CH2:28][CH2:29][CH2:30][C:31]([O:33][CH3:34])=[O:32]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 107604Methyl 4-bromobutyrateHCID 179535512-Methyl-4-(2-{4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl}ethyl)phenol2×

Product 1

HCID 17972182Methyl 4-[2-methyl-4-(2-{4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl}ethyl)phenoxy]butanoate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 2-methyl-4-(2-{4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl}ethyl)phenol (intermediate 7, 0.08 g ) in acetonitrile (2 ml) was added methyl 4-bromobutyrate (0.090 g) and cesium carbonate (0.194 g). The mixture was stirred at room temperature for 24 hours then partitioned between water and ethyl acetate. The organic layer was dried, the solvent removed and the resulting oil was purified by SPE(Si cartridge). Elution with cyclohexane:ethyl acetate (20:1) gave the title compound as an oil which crystallised on standing.

Workup

  1. customthen partitioned between water and ethyl acetate
  2. customThe organic layer was dried
  3. customthe solvent removed
  4. customthe resulting oil was purified by SPE(Si cartridge)
  5. washElution with cyclohexane:ethyl acetate (20:1)

Sources & evidence

ORD record
ord-49107c50bdbf404185de1facdf46942b
Source dataset
uspto-grants-2007_03
Patent number
US07196107B2

Reaction notes

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