Sodium sulfate decahydrate → 6-(Benzyloxy)quinoline-2-carbaldehyde

HRID 1497557Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1497557
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[N:15]=[C:14]([C:19](OCC1C=CC=CC=1)=[O:20])[CH:13]=[CH:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].C([Al+]CC(C)C)C(C)C.O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1.C1(C)C=CC=CC=1>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[N:15]=[C:14]([CH:19]=[O:20])[CH:13]=[CH:12]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

6

Edukt 3

HCID 62649Sodium sulfate decahydrateHCID 21225700DiisobutylaluminumhydrideHCID 90282113Benzyl 6-(benzyloxy)quinoline-2-carboxylate

Produkt 1

HCID 902819596-(Benzyloxy)quinoline-2-carbaldehydeAusbeute 36,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

To a solution of benzyl 6-(benzyloxy)quinoline-2-carboxylate (650 mg) in tetrahydrofuran (13.0 mL) was added a 1 M solution diisobutylaluminum hydride in toluene (2.64 mL) at −78° C., followed by stirring at −78° C. for 1 hour. To the reaction mixture was added sodium sulfate decahydrate (680 mg), followed by stirring at room temperature overnight. The insoluble material was collected by filtration and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-ethyl acetate) to obtain 6-(benzyloxy)quinoline-2-carbaldehyde (170 mg).

Aufarbeitung

  1. stirringby stirring at room temperature overnight
  2. filtrationThe insoluble material was collected by filtration
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-41cbf27534be47d4b13c5eb0206cb237
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09199927B2

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