Water → 3-[4-Methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-yl]-propan-1-ol

HRID 1767893

Reaktionsgleichung

Reaktionsgleichung von HRID 1767893
C([O:3][C:4](=O)[CH2:5][CH2:6][C:7]1[S:11][C:10]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=2)=[N:9][C:8]=1[CH3:22])C.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[CH3:22][C:8]1[N:9]=[C:10]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=2)[S:11][C:7]=1[CH2:6][CH2:5][CH2:4][OH:3]

Komponenten

6

Edukt 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 692796933-[4-Methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-yl]-propionic acid ethyl ester

Produkt 1

HCID 236144873-[4-Methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-yl]-propan-1-olAusbeute 69 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A solution of 3-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-yl]-propionic acid ethyl ester (470 mg, 1.4 mmol) in tetrahydrofuran (5 ml) was added to a suspension of lithium aluminum hydride (53 mg, 1.4 mmol) in tetrahydrofuran (5 ml) under an argon atmosphere at ambient temperature within 5 min. The mixture was stirred for 5 h, cooled to 0° C. and treated cautiously with water (5 ml) and 10% aqueous NaOH (1 ml). The reaction mixture was filtered over celite, ice water/ethyl acetate 1/1 was added and the layers were separated. The aqueous layer was extracted one more time with ethyl acetate, the combined organic layers were washed with ice water/brine 1/1 and dried over sodium sulfate. Removal of the solvent under reduced pressure gave a yellow oil which was purified by column chromatography (silica gel, heptane/AcOEt) to yield 285 mg (950 μmol, 69%) of the title compound as colorless oil.

Aufarbeitung

  1. filtrationThe reaction mixture was filtered over celite, ice water/ethyl acetate 1/1
  2. additionwas added
  3. customthe layers were separated
  4. extractionThe aqueous layer was extracted one more time with ethyl acetate
  5. washthe combined organic layers were washed with ice water/brine 1/1
  6. dry with materialdried over sodium sulfate
  7. customRemoval of the solvent under reduced pressure
  8. customgave a yellow oil which
  9. customwas purified by column chromatography (silica gel, heptane/AcOEt)

Quellen und Nachweise

ORD-Eintrag
ord-61c6d8e858914f298ec579be14178bb8
Quelldatensatz
uspto-grants-2007_06
Patentnummer
US07235572B2

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