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Diisobutylaluminumhydride → HCID 22010670, Verbindung

HRID 323173
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 323173
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:14]([NH:16][C:17]3[CH:41]=[CH:40][C:20]([C:21]([N:23]([CH3:39])[C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[O:30][CH2:31][CH2:32][CH2:33][C:34](OCC)=[O:35])=[O:22])=[CH:19][CH:18]=3)=[O:15])=[CH:10][CH:11]=[CH:12][CH:13]=2)=[CH:4][CH:3]=1.[H-].C([Al+]CC(C)C)C(C)C>ClCCl.C1(C)C=CC=CC=1>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:9]([C:14]([NH:16][C:17]3[CH:18]=[CH:19][C:20]([C:21]([N:23]([CH3:39])[C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[O:30][CH2:31][CH2:32][CH2:33][CH:34]=[O:35])=[O:22])=[CH:40][CH:41]=3)=[O:15])=[CH:10][CH:11]=[CH:12][CH:13]=2)=[CH:6][CH:7]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 21225700DiisobutylaluminumhydrideHCID 22010702HCID 22010702, Verbindung

Produkt 1

HCID 22010670HCID 22010670, VerbindungAusbeute 97,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 4-(4′-methylbiphenyl-2-carboxamido)-N-methyl-N-[2-(3-ethoxycarbonylprop-1-yloxy)phenyl]benzamide (1.10 g) in dichloromethane (20 ml) was added dropwise a solution of diisobutylaluminum hydride in toluene (1.5 M solution, 2 ml) at −78° C. and the mixture was stirred at the same temperature for 2 hours. The reaction was quenched with addition of water and the resulting mixture was warmed to ambient temperature. The mixture was extracted with dichloromethane and the organic phase was washed successively with 1N hydrochloric acid, water and brine. The organic solution was dried over magnesium sulfate and the solvent was evaporated in vacuo to give 4-(4′-methylbiphenyl-2-carboxamido)-N-methyl-N-[2-(3-formylprop-1-yloxy)phenyl]benzamide (987 mg) as a syrup. The unstable aldehyde was immediately used for next step.

Aufarbeitung

  1. customThe reaction was quenched with addition of water
  2. extractionThe mixture was extracted with dichloromethane
  3. washthe organic phase was washed successively with 1N hydrochloric acid, water and brine
  4. dry with materialThe organic solution was dried over magnesium sulfate
  5. customthe solvent was evaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-a63bc6ff62534a929dfa3198dd730796
Quelldatensatz
uspto-grants-2001_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06211242B1

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