Acetaldehyde → 2,3,4-trifluoro-6-(1-hydroxyethyl)-5-pivaloylamino-O-tetrahydropyranylphenol

HRID 1736250Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1736250
[F:1][C:2]1[C:7]([F:8])=[C:6]([F:9])[C:5]([NH:10][C:11](=[O:16])[C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:4][C:3]=1[O:17][CH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][O:19]1.C([Li])CCC.[CH:29](=[O:31])[CH3:30].O>O1CCCC1.CCCCCC>[F:1][C:2]1[C:7]([F:8])=[C:6]([F:9])[C:5]([NH:10][C:11](=[O:16])[C:12]([CH3:15])([CH3:14])[CH3:13])=[C:4]([CH:29]([OH:31])[CH3:30])[C:3]=1[O:17][CH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][O:19]1

Komponenten

7

Edukt 4

HCID 177AcetaldehydeHCID 962WaterHCID 867496582,3,4-trifluoro-5-pivaloylamino-O-tetrahydropyranylphenolHCID 178418339Butyllithium

Produkt 1

HCID 867496592,3,4-trifluoro-6-(1-hydroxyethyl)-5-pivaloylamino-O-tetrahydropyranylphenolAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8058HexaneLösungsmittel

Reaktionsbedingungen

Temperatur
-35 °C

Versuchsvorschrift

3.60 g (10.9 mmol) of the above 2,3,4-trifluoro-5-pivaloylamino-O-tetrahydropyranylphenol was dissolved in 50 mL of tetrahydrofuran, 14 mL of a 1.6 M solution of n-butyl lithium in n-hexane was added dropwise to the solution at an internal temperature of -60° C. or below, the mixture was warmed to -35° C. and cooled again to -60° C. or below. About 2 mL of acetaldehyde was added thereto in a gaseous condition and the mixture was stirred for 20 minutes. Water was added to the reaction solution, the mixture was warmed to room temperature and extracted once with ethyl acetate. The organic layer was washed once with water and once with an aqueous saturated solution of sodium chloride and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=5:1-3:1) to give 2.45 g of a mixture of diastereomers of 2,3,4-trifluoro-6-(1-hydroxyethyl)-5-pivaloylamino-O-tetrahydropyranylphenol (yield: 60%).

Aufarbeitung

  1. temperaturecooled again to -60° C. or below
  2. temperaturethe mixture was warmed to room temperature
  3. extractionextracted once with ethyl acetate
  4. washThe organic layer was washed once with water and once with an aqueous saturated solution of sodium chloride
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=5:1-3:1)

Quellen und Nachweise

ORD-Eintrag
ord-fe9ddd7490bf4de2a60bb58e47a75f65
Quelldatensatz
uspto-grants-1996_07
Patentnummer
US05539112

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