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Aluminium lithium hydride → {2-[4-(Trifluoromethyl)phenyl]-1,3-oxazol-4-yl}methanol

HRID 585069
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 585069
[F:1][C:2]([F:19])([F:18])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:10][CH:11]=[C:12]([C:14](OC)=[O:15])[N:13]=2)=[CH:5][CH:4]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[F:19][C:2]([F:1])([F:18])[C:3]1[CH:4]=[CH:5][C:6]([C:9]2[O:10][CH:11]=[C:12]([CH2:14][OH:15])[N:13]=2)=[CH:7][CH:8]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 21226445Aluminium lithium hydrideHCID 22064320Methyl 2-(4-(trifluoromethyl)phenyl)oxazole-4-carboxylate

Produkt 1

HCID 22064105{2-[4-(Trifluoromethyl)phenyl]-1,3-oxazol-4-yl}methanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A solution of methyl 2-[4-(trifluoromethyl)phenyl]-1,3-oxazole-4-carboxylate (1.365 mmol) in tetrahydrofuran (20 ml) was cooled to 0° C., and lithium aluminum hydride in tetrahydrofuran (1.365 mmol) was added dropwise. The reaction mixture was stirred at 0° C. for 30 minutes, slowly quenched with water, followed by addition of ammonium chloride solution. The resulting mixture was filtered through celite, and washed with ethyl acetate. The filtrate was washed with brine, dried over sodium sulfate, and solvent removed under reduced pressure. The residue was purified by chromatography, to yield {2-[4-(trifluoromethyl)phenyl]-1,3-oxazol-4-yl}methan-1-ol, a compound of formula (16).

Aufarbeitung

  1. customslowly quenched with water
  2. additionfollowed by addition of ammonium chloride solution
  3. filtrationThe resulting mixture was filtered through celite
  4. washwashed with ethyl acetate
  5. washThe filtrate was washed with brine
  6. dry with materialdried over sodium sulfate, and solvent
  7. customremoved under reduced pressure
  8. customThe residue was purified by chromatography

Quellen und Nachweise

ORD-Eintrag
ord-95a36d3e4df243e68f8c87cb79d836a2
Quelldatensatz
uspto-grants-2005_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06930111B2

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