Ammonium Chloride → (E)-3-(6-methyl-2-naphthyl)-2-buten-1-ol

HRID 2229245Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2229245
[H-].C([Al+]CC(C)C)C(C)C.[CH3:11][C:12]1[CH:13]=[C:14]2[C:19](=[CH:20][CH:21]=1)[CH:18]=[C:17](/[C:22](/[CH3:29])=[CH:23]/[C:24](OCC)=[O:25])[CH:16]=[CH:15]2.[NH4+].[Cl-]>C1(C)C=CC=CC=1.C1COCC1>[CH3:11][C:12]1[CH:13]=[C:14]2[C:19](=[CH:20][CH:21]=1)[CH:18]=[C:17](/[C:22](/[CH3:29])=[CH:23]/[CH2:24][OH:25])[CH:16]=[CH:15]2

Komponenten

6

Edukt 3

HCID 25517Ammonium ChlorideHCID 21225700DiisobutylaluminumhydrideHCID 86758349ethyl (E)-3-(6-methyl-2-naphthyl)crotonate

Produkt 1

HCID 18467042(E)-3-(6-methyl-2-naphthyl)-2-buten-1-olAusbeute 84,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

A solution of diisobutylaluminum hydride in toluene (1.5M, 30 ml) was added dropwise to a solution of ethyl (E)-3-(6-methyl-2-naphthyl)crotonate (3.62 g) in THF (50 ml) at −78° C. and the mixture was stirred at −78° C. for 15 minutes. Saturated aqueous solution of NH4Cl was added to the mixture and organic layer was washed with 1N HCl and brine, dried and concentrated. The residue was crystallized from hexane-cyclohexane gave the titled compound (2.54 g) as a colorless solid.

Aufarbeitung

  1. washwas washed with 1N HCl and brine
  2. customdried
  3. concentrationconcentrated
  4. customThe residue was crystallized from hexane-cyclohexane

Quellen und Nachweise

ORD-Eintrag
ord-9588ffe7f37e4c1986c2b8f8b9438f10
Quelldatensatz
uspto-grants-2002_07
Patentnummer
US06420375B1

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