Cesium carbonate → 2-{4-[2-Methoxymethyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-ylmethoxy]-2-methyl-phenoxy}-2-methyl-propionic acid ethyl ester

HRID 1242366Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1242366
[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]([CH2:36][O:37][CH3:38])=[N:22][C:23]([C:26]2[CH:31]=[CH:30][C:29]([C:32]([F:35])([F:34])[F:33])=[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]([O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:19][C:20]2[C:21]([CH2:36][O:37][CH3:38])=[N:22][C:23]([C:26]3[CH:27]=[CH:28][C:29]([C:32]([F:35])([F:33])[F:34])=[CH:30][CH:31]=3)=[CH:24][CH:25]=2)=[CH:11][C:10]=1[CH3:16])([CH3:6])[CH3:7])[CH3:2]

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 16756990Ethyl 2-(4-hydroxy-2-methylphenoxy)-2-methylpropanoateHCID 219356963-Chloromethyl-2-methoxymethyl-6-(4-trifluoromethyl-phenyl)-pyridine

Produkt 1

HCID 670723042-{4-[2-Methoxymethyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-ylmethoxy]-2-methyl-phenoxy}-2-methyl-propionic acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To 0.097 g (0.407 mmol) of 2-(4-hydroxy-2-methyl-phenoxy)-2-methyl-propionic acid ethyl ester (described in WO 02/092590) and 0.145 g (0.459 mmol) of the above prepared 3-chloromethyl-2-methoxymethyl-6-(4-trifluoromethyl-phenyl)-pyridine, dissolved in 2.5 ml of abs. acetonitrile, was added 0.180 g of Cs2CO3 (0.552 mmol). The reaction was stirred for 22 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), gave 0.214 g of pure title compound as colorless oil.

Aufarbeitung

  1. dissolutiondissolved in 2.5 ml of abs
  2. additionPouring
  3. extractionextraction with AcOEt
  4. washwashing with water and brine
  5. dry with materialdrying over magnesium sulfate, and evaporation of the solvents

Quellen und Nachweise

ORD-Eintrag
ord-2f6bc060423240dba46fc17cb2f8c68e
Quelldatensatz
uspto-grants-2006_10
Patentnummer
US07115611B2

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