Methyl 7-chloronaphthalene-1-carboxylate → HCID 68697042, Verbindung

HRID 1876279Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1876279
[H-].C([Al+]CC(C)C)C(C)C.C[O:12][C:13]([C:15]1[C:24]2[C:19](=[CH:20][CH:21]=[C:22]([Cl:25])[CH:23]=2)[CH:18]=[CH:17][CH:16]=1)=O>C(Cl)Cl>[Cl:25][C:22]1[CH:23]=[C:24]2[C:19]([CH:18]=[CH:17][CH:16]=[C:15]2[CH2:13][OH:12])=[CH:20][CH:21]=1

Komponenten

4

Edukt 2

HCID 230778Methyl 7-chloronaphthalene-1-carboxylateHCID 21225700Diisobutylaluminumhydride

Produkt 1

HCID 68697042HCID 68697042, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A 0.7M diisobutylaluminium hydride solution in CH2Cl2 is added dropwise at −78° to 22 g of 7-chloro-naphthalene-1-carboxylic acid methyl ester in CH2Cl2. After stirring at −78° for 1 hour, the mixture obtained is warmed up to 0°, quenched with aq. 10% sodium tartrate solution and stirred for further few minutes. The organic phase obtained is separated, washed with brine, dried and solvent is evaporated. The residue obtained is purified by flash chromatography on silica gel (eluent: cyclohexane/EtOAc 8/1 to 4/1) and the title compound is obtained.

Aufarbeitung

  1. customthe mixture obtained
  2. temperatureis warmed up to 0°
  3. customquenched with aq. 10% sodium tartrate solution
  4. stirringstirred for further few minutes
  5. customThe organic phase obtained
  6. customis separated
  7. washwashed with brine
  8. customdried
  9. customsolvent is evaporated
  10. customThe residue obtained
  11. customis purified by flash chromatography on silica gel (eluent: cyclohexane/EtOAc 8/1 to 4/1)

Quellen und Nachweise

ORD-Eintrag
ord-12f7825e0b1f4576a975f938b8d70ccf
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08309596B2

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