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

HRID 2261084

Reaktionsgleichung

Reaktionsgleichung von HRID 2261084
CO[C:3]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[N:11]=[CH:10]N=[C:8]2[Cl:15])=[O:4].[CH3:16]C(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:4])[CH:6]=2)[N:11]=[CH:10][CH:16]=1

Komponenten

4

Edukt 2

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

Produkt 1

HCID 57469641(4-Chloroquinolin-6-yl)methanolAusbeute 66 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-10 °C

Versuchsvorschrift

To a solution of methyl-4-chloroquinazoline-6-carboxylate (3.5 g, 0015 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-chloroquinoline-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-d4d4fdbbdfd34863a9f143cfbff3d516
Quelldatensatz
uspto-grants-2010_12
Patentnummer
US07846925B2

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