Cesium carbonate → HCID 67072212, compound

HRID 1242343Notes

Reaction equation

HRID 1242343 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]([O:32][C:33]([F:36])([F:35])[F:34])=[CH:28][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]([CH3:6])([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]([O:32][C:33]([F:36])([F:34])[F:35])=[CH:28][CH:27]=3)=[CH:24][CH:25]=2)=[CH:11][C:10]=1[CH3:16])[CH3:7])[CH3:2]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 16756990Ethyl 2-(4-hydroxy-2-methylphenoxy)-2-methylpropanoateHCID 219357213-Chloromethyl-2-methyl-6-(4-trifluoromethoxy-phenyl)-pyridine

Product 1

HCID 67072212HCID 67072212, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To 0.123 g (0.516 mmol) of 2-(4-hydroxy-2-methyl-phenoxy)-2-methyl-propionic acid ethyl ester (described in WO 02/092590) and 0.163 g (0.540 mmol) of the above prepared 3-chloromethyl-2-methyl-6-(4-trifluoromethoxy-phenyl)-pyridine, dissolved in 4.7 ml of abs. acetonitrile, was added 0.184 g of Cs2CO3 (0.565 mmol). The reaction was stirred over night at ambient temperature. Pouring onto crashed ice/NH4Cl-solution, twofold extraction with AcOEt, washing with water, drying over sodium sulfate, and evaporation of the solvents, followed by flash chromatography (SiO2, hexane/AcOEt=8/2) yielded 0.243 g of pure title compound as colorless oil.

Workup

  1. dissolutiondissolved in 4.7 ml of abs
  2. additionPouring
  3. extractionextraction with AcOEt
  4. washwashing with water
  5. dry with materialdrying over sodium sulfate, and evaporation of the solvents

Sources & evidence

ORD record
ord-fde4861cef564b21ae10f351fc3d9645
Source dataset
uspto-grants-2006_10
Patent number
US07115611B2

Reaction notes

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