Aluminium lithium hydride → 2-[5-Methyl-2-(4-trifluoromethyl-phenyl)-thiazol-4-yl]-ethanol

HRID 1869284Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1869284
[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:9][C:10](=O)[CH2:11][C:12]1[N:13]=[C:14]([C:18]2[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][CH:19]=2)[S:15][C:16]=1[CH3:17])C>C1COCC1>[OH:9][CH2:10][CH2:11][C:12]1[N:13]=[C:14]([C:18]2[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][CH:19]=2)[S:15][C:16]=1[CH3:17]

Komponenten

4

Edukt 2

HCID 21226445Aluminium lithium hydrideHCID 57986743[5-Methyl-2-(4-trifluoromethyl-phenyl)-thiazol-4-yl]acetic acid ethyl ester

Produkt 1

HCID 226474902-[5-Methyl-2-(4-trifluoromethyl-phenyl)-thiazol-4-yl]-ethanolAusbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
5 °C

Versuchsvorschrift

Cool (0° C.) a solution of lithium aluminum hydride (5.3 mL, 1M in THF) and add a solution of [5-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-4-yl]-acetic acid ethyl ester (Example 1, 1.4g, 4.25 mmol) in THF (15 mL). On complete addition, remove the cold bath and stir for 2 hrs. Cool this solution to 5° C., and then add water (0.2 mL), dropwise, followed by NaOH solution (0.2 mL, 5M in water) and water (0.2 mL). Dilute the resulting mixture with ethyl acetate and then filter through a pad of celite. Wash the solids with dichloromethane and then concentrate the combined filtrates under reduced pressure. Purify the residue by flash chromatography (elute with 30% ethyl acetate 40% dichloromethane in heptane) to give the title compound as a yellow solid (0.879 g) Use the compound of Example 1 as the starting material to obtain the title compound.

Aufarbeitung

  1. additionOn complete addition
  2. customremove the cold bath
  3. additionDilute the resulting mixture with ethyl acetate
  4. filtrationfilter through a pad of celite
  5. washWash the solids with dichloromethane
  6. concentrationconcentrate the combined filtrates under reduced pressure
  7. customPurify the residue
  8. washby flash chromatography (elute with 30% ethyl acetate 40% dichloromethane in heptane)

Quellen und Nachweise

ORD-Eintrag
ord-cf36f2be84304fcbbfcf53f31efe3f5c
Quelldatensatz
uspto-grants-2009_12
Patentnummer
US07638539B2

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