Water → (rac.) 4-(4-Chloro-3-fluoro-2-methoxyphenyl)-4-methyl-2-(trifluoromethyl)-2-hydroxy-pentanoic acid ethyl ester

HRID 420636Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 420636
[CH2:1]([O:3][C:4](=[O:29])[C:5]([C:25]([F:28])([F:27])[F:26])([O:20][Si](C)(C)C)[CH2:6][C:7]([C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[C:12]([F:17])[C:11]=1[O:18][CH3:19])([CH3:9])[CH3:8])[CH3:2].O.O.O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O>O1CCCC1>[CH2:1]([O:3][C:4](=[O:29])[C:5]([C:25]([F:27])([F:26])[F:28])([OH:20])[CH2:6][C:7]([C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[C:12]([F:17])[C:11]=1[O:18][CH3:19])([CH3:9])[CH3:8])[CH3:2]

Komponenten

5

Edukt 3

HCID 962WaterHCID 11726816Tetrabutylammonium Fluoride TrihydrateHCID 17989278(Rac.) 4-(4-chloro-3-fluoro-2-methoxyphenyl)-4-methyl-2-(trifluoromethyl)-2-trimethylsilyloxy-pentanoic acid ethyl ester

Produkt 1

HCID 17989096(rac.) 4-(4-Chloro-3-fluoro-2-methoxyphenyl)-4-methyl-2-(trifluoromethyl)-2-hydroxy-pentanoic acid ethyl esterAusbeute 77,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

4.71 g (10.26 mmol) of (rac.) 4-(4-chloro-3-fluoro-2-methoxyphenyl)-4-methyl-2-(trifluoromethyl)-2-trimethylsilyloxy-pentanoic acid ethyl ester is dissolved in 57 ml of tetrahydrofuran and mixed with 3.24 g (10.26 mmol) of tetrabutylammonium fluoride trihydrate: after stirring over the weekend at room temperature, the reaction mixture is mixed with water and extracted three times with methyl-tert-butyl ether. The combined organic extracts are washed with brine. After drying, the solvent is spun off, and the remaining residue is chromatographed on silica gel (mobile solvent ethyl acetate/hexane). 3.07 g (77.4%) of the desired compound is isolated.

Aufarbeitung

  1. extractionextracted three times with methyl-tert-butyl ether
  2. washThe combined organic extracts are washed with brine
  3. customAfter drying
  4. customthe remaining residue is chromatographed on silica gel (mobile solvent ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-87c643c5f0b5439fb1ce0b8e706007f1
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08097627B2

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