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4-(5-Fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-trifluoromethylpentanoic acid ethyl ester → 2-Hydroxy-4-(5-fluoro-2-methoxyphenyl)-4-methyl-2-trifluoromethyl-pentanol

HRID 916001
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 916001
C([O:3][C:4](=O)[C:5]([OH:23])([C:19]([F:22])([F:21])[F:20])[CH2:6][C:7]([C:10]1[CH:15]=[C:14]([F:16])[CH:13]=[CH:12][C:11]=1[O:17][CH3:18])([CH3:9])[CH3:8])C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[F:16][C:14]1[CH:13]=[CH:12][C:11]([O:17][CH3:18])=[C:10]([C:7]([CH3:9])([CH3:8])[CH2:6][C:5]([C:19]([F:21])([F:22])[F:20])([OH:23])[CH2:4][OH:3])[CH:15]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 179356104-(5-Fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-trifluoromethylpentanoic acid ethyl esterHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 219489282-Hydroxy-4-(5-fluoro-2-methoxyphenyl)-4-methyl-2-trifluoromethyl-pentanolAusbeute 92,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a chilled solution (ice-water bath) of 6 g (17.0 mmol) of the above 4-(5-fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-trifluoromethylpentanoic acid ethyl ester in 60 mL of dry THF, 2.4 g (61.5 mmol) of lithium aluminum hydride was added in portions. After the addition, the cold bath was removed and the mixture was stirred at room temperature overnight. The mixture was then warmed at reflux for 3 hours and then cautiously quenched by slow addition to 100 mL of THF containing 2 mL of water. Additional water was then cautiously added for a total of 15 mL and the resulting mixture stirred for 2 hours. The water was removed by drying over magnesium sulfate and 300 mL of EtOAc was added. After 1 hour, the mixture was filtered through diatomaceous earth and concentrated in vacuo to afford 4.9 g (92%) of 4-(5-fluoro-2-methoxyphenyl)-4-methyl-2-trifluoromethylpentane-1,2-diol as an oil.

Aufarbeitung

  1. additionAfter the addition
  2. customthe cold bath was removed
  3. temperatureThe mixture was then warmed
  4. temperatureat reflux for 3 hours
  5. customcautiously quenched by slow addition to 100 mL of THF containing 2 mL of water
  6. additionAdditional water was then cautiously added for a total of 15 mL
  7. stirringthe resulting mixture stirred for 2 hours
  8. customThe water was removed
  9. dry with materialby drying over magnesium sulfate and 300 mL of EtOAc
  10. additionwas added
  11. waitAfter 1 hour
  12. filtrationthe mixture was filtered through diatomaceous earth
  13. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-6cfca9cb3d17467fad3631603509bc79
Quelldatensatz
uspto-grants-2007_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07268152B2

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