Cesium carbonate → HCID 67072404, compound

HRID 1242339Notes

Reaction equation

HRID 1242339 reaction equation
[CH2:1]([O:3][C:4](=[O:17])[C:5]([O:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][C:10]=1[CH3:16])([CH3:7])[CH3:6])[CH3:2].Cl[CH2:19][C:20]1[C:21]([CH3:37])=[N:22][C:23]([C:26]2[CH:31]=[CH:30][C:29]([C:32]([F:35])([F:34])[F:33])=[C:28]([F:36])[CH:27]=2)=[CH:24][CH:25]=1.C([O-])([O-])=O.[Cs+].[Cs+]>C(#N)C>[CH2:1]([O:3][C:4](=[O:17])[C:5]([O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:19][C:20]2[C:21]([CH3:37])=[N:22][C:23]([C:26]3[CH:31]=[CH:30][C:29]([C:32]([F:34])([F:35])[F:33])=[C:28]([F:36])[CH:27]=3)=[CH:24][CH:25]=2)=[CH:11][C:10]=1[CH3:16])([CH3:6])[CH3:7])[CH3:2]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 16756990Ethyl 2-(4-hydroxy-2-methylphenoxy)-2-methylpropanoateHCID 21935666HCID 21935666, compound

Product 1

HCID 67072404HCID 67072404, compoundYield 74.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To 0.139 g (0.583 mmol) of 2-(4-hydroxy-2-methyl-phenoxy)-2-methyl-propionic acid ethyl ester (described in WO 02/092590) and 0.177 g (0.583 mmol) of 3-chloromethyl-6-(3-fluoro-4-trifluoromethyl-phenyl)-2-methyl-pyridine (example 38C]), dissolved in 3 ml of abs. acetonitrile, was added 0.228 g of Cs2CO3 (0.700 mmol). The reaction mixture was stirred during 3 h at ambient temperature. Pouring onto crashed ice/NH4Cl-solution, twofold extraction with AcOEt, washing with water and brine, drying over magnesium sulfate, and evaporation of the solvents, followed by flash chromatography (SiO2, hexane/AcOEt=88/12) yielded 0.219 g of pure title compound as white solid.

Workup

  1. additionPouring
  2. extractionextraction with AcOEt
  3. washwashing with water and brine
  4. dry with materialdrying over magnesium sulfate, and evaporation of the solvents

Sources & evidence

ORD record
ord-0eb232f9ad7547dfac998f5034094d08
Source dataset
uspto-grants-2006_10
Patent number
US07115611B2

Reaction notes

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