Diisobutylaluminum hydride → (4-Chloroquinazolin-6-yl)methanol

HRID 425763

Reaktionsgleichung

Reaktionsgleichung von HRID 425763
C[O:2][C:3]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[N:11]=[CH:10][N:9]=[C:8]2[Cl:15])=O.CC(C[AlH]CC(C)C)C>C1COCC1>[Cl:15][C:8]1[C:7]2[C:12](=[CH:13][CH:14]=[C:5]([CH2:3][OH:2])[CH:6]=2)[N:11]=[CH:10][N:9]=1

Komponenten

4

Edukt 2

HCID 14487Diisobutylaluminum hydrideHCID 18925080Methyl 4-chloroquinazoline-6-carboxylate

Produkt 1

HCID 57469640(4-Chloroquinazolin-6-yl)methanolAusbeute 68,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-10 °C

Versuchsvorschrift

To a solution of methyl-4-chloroquinazoline-6-carboxylate (3.5 g, 0.015 mol) in dry THF (35 mL) at −25° C. was added DIBAL-H (4.4 g, 0.031 mol) and stirred at −25° C. to RT for 2 h. The reaction mixture was cooled to −10° C. and quenched with 10% aqueous NaHCO3 (9 mL). The reaction mixture was extracted with ethylacetate (100 mL), washed with water, brine and dried. The solvent was removed under vacuum to give 4-chloroquinazoline-6-yl methanol (2 g, 66%).

Aufarbeitung

  1. customquenched with 10% aqueous NaHCO3 (9 mL)
  2. extractionThe reaction mixture was extracted with ethylacetate (100 mL)
  3. washwashed with water, brine
  4. customdried
  5. customThe solvent was removed under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-ebf3c2ba782f47bf838d1fa2bf29ff02
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08106214B2

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