Aluminium lithium hydride → (4-Ethylthiazol-5-yl)methanol

HRID 577233Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 577233
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([C:9]1[N:10]=[CH:11][S:12][C:13]=1[C:14](OCC)=[O:15])[CH3:8]>C1COCC1>[CH2:7]([C:9]1[N:10]=[CH:11][S:12][C:13]=1[CH2:14][OH:15])[CH3:8]

Komponenten

4

Edukt 2

HCID 21226445Aluminium lithium hydrideHCID 53421078Ethyl 4-ethylthiazole-5-carboxylate

Produkt 1

HCID 59589347(4-Ethylthiazol-5-yl)methanolAusbeute 79,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a 0° C. mixture of lithium aluminum hydride (1.2 g, 31.2 mmol) in anhydrous THF (30 mL) was slowly added a solution of ethyl 4-ethyl-1,3-thiazole-5-carboxylate (3.19 g, 15.6 mmol) in anhydrous THF (40 mL). The reaction mixture was stirred at 0° C. for 1.5 hours. The reaction was quenched with 5 N NaOH. Water (100 mL) and EtOAc (100 mL) were added. The mixture was stirred for 30 minutes. The solid material was removed by filtration. The organic layer was recovered. The aqueous layer was extracted with EtOAc (1×100 mL). The combined organic extracts were dried over MgSO4, filtered, evaporated, and dried in vacuo, affording (4-ethyl-1,3-thiazol-5-yl)methanol (1.77 g, 79% yield). The product was used without further purification.

Aufarbeitung

  1. customThe reaction was quenched with 5 N NaOH
  2. additionWater (100 mL) and EtOAc (100 mL) were added
  3. stirringThe mixture was stirred for 30 minutes
  4. customThe solid material was removed by filtration
  5. customThe organic layer was recovered
  6. extractionThe aqueous layer was extracted with EtOAc (1×100 mL)
  7. dry with materialThe combined organic extracts were dried over MgSO4
  8. filtrationfiltered
  9. customevaporated
  10. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-f5ec07bd48244383a0f4e6ee005e9634
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09040538B2

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