Cesium carbonate → 2-Hydroxy-4-(4-iodo-2-methoxyphenyl)-4-methyl-2-trifluoromethyl-valeric acid methyl ester

HRID 1443202Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1443202
[CH3:1][O:2][C:3](=[O:19])[C:4](=[O:18])[CH2:5][C:6]([C:9]1[CH:14]=[CH:13][C:12]([I:15])=[CH:11][C:10]=1[O:16][CH3:17])([CH3:8])[CH3:7].[F:20][C:21]([Si](C)(C)C)([F:23])[F:22].C(=O)([O-])[O-].[Cs+].[Cs+].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>CN(C=O)C.O>[CH3:1][O:2][C:3](=[O:19])[C:4]([OH:18])([C:21]([F:23])([F:22])[F:20])[CH2:5][C:6]([C:9]1[CH:14]=[CH:13][C:12]([I:15])=[CH:11][C:10]=1[O:16][CH3:17])([CH3:8])[CH3:7]

Komponenten

7

Edukt 4

HCID 10796Cesium carbonateHCID 552549(Trifluoromethyl)trimethylsilaneHCID 2724141Tetrabutylammonium FluorideHCID 686789254-(4-Iodo-2-methoxyphenyl)-4-methyl-2-oxovaleric acid methyl ester

Produkt 1

HCID 179892492-Hydroxy-4-(4-iodo-2-methoxyphenyl)-4-methyl-2-trifluoromethyl-valeric acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

3 g of 4-(4-iodo-2-methoxyphenyl)-4-methyl-2-oxovaleric acid (WO 98/54159) is added in a solution of 1.3 ml of thionyl chloride in 12 ml of methanol at 0° C. and stirred for 10 hours at room temperature. It is added to saturated bicarbonate solution and extracted with ethyl acetate. The organic phase is washed with bicarbonate solution and brine, dried (Na2SO4) and concentrated by evaporation. 3.2 g of 4-(4-iodo-2-methoxyphenyl)-4-methyl-2-oxovaleric acid methyl ester is obtained as a crude product. This ester is mixed with 4.5 ml of trifluoromethyltrimethylsilane in 70 ml of DMF and 1.63 g of cesium carbonate at 0° C. and stirred for 10 hours at room temperature. 20 mg of tetrabutylammonium fluoride is added, and it is stirred for another 30 minutes at room temperature. The batch is added to water and extracted with ethyl acetate. The organic phase is washed with water and brine, dried (Na2SO4) and concentrated by evaporation. After chromatography on silica gel (hexane/ethyl acetate 0->15%), 1.47 g of the title compound is obtained as a yellow oil.

Aufarbeitung

  1. stirringit is stirred for another 30 minutes at room temperature
  2. extractionextracted with ethyl acetate
  3. washThe organic phase is washed with water and brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated by evaporation

Quellen und Nachweise

ORD-Eintrag
ord-efced3f8bce641c193029ec70a9355cf
Quelldatensatz
uspto-grants-2010_02
Patentnummer
US07659297B2

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