Hexane → HCID 131718352, Verbindung

HRID 22132Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 22132
C([Li])CCC.CCCCCC.[C:12]([O:16][C:17]([NH:19][CH:20]1[CH2:29][CH2:28][C:27]2[C:22](=[CH:23][CH:24]=[C:25]([Br:30])[CH:26]=2)[CH2:21]1)=[O:18])([CH3:15])([CH3:14])[CH3:13].[N:31]1[CH:36]=[CH:35][CH:34]=[C:33]([CH:37]=[O:38])[CH:32]=1>O1CCCC1>[C:12]([O:16][C:17]([NH:19][CH:20]1[CH2:29][CH2:28][C:27]2[CH2:26][C:25]([CH:37]([C:33]3[CH:32]=[N:31][CH:36]=[CH:35][CH:34]=3)[OH:38])([Br:30])[CH:24]=[CH:23][C:22]=2[CH2:21]1)=[O:18])([CH3:15])([CH3:13])[CH3:14]

Komponenten

6

Edukt 4

HCID 8058HexaneHCID 103713-PyridinecarboxaldehydeHCID 10064926tert-butyl N-(6-bromo-1,2,3,4-tetrahydronaphthalen-2-yl)carbamateHCID 178418339Butyllithium

Produkt 1

HCID 131718352HCID 131718352, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-70 °C

Versuchsvorschrift

8.8 ml of a solution of n-butyl lithium in hexane (2.5 mol) was dropped to a solution of 3.25 g of 2-tert.butoxycarbonylamino-6-bromo-1,2,3,4-tetrahydro-naphthaline in 50 ml of absolute tetrahydrofurane cooled to -70° C. and stirring was continued for 1.5 hours at -50° C. Subsequently, 1.1 g of pyridine-3-aldehyde were dropped into the mixture at -70° C. After stirring for one hour, the reaction mixture was poured on ice and extracted with ethyl acetate. The organic phase was washed with water, dried and evaporated. The obtained residue was recrystallised from cyclohexane/ethyl acetate.

Aufarbeitung

  1. stirringAfter stirring for one hour
  2. additionthe reaction mixture was poured on ice
  3. extractionextracted with ethyl acetate
  4. washThe organic phase was washed with water
  5. customdried
  6. customevaporated
  7. customThe obtained residue was recrystallised from cyclohexane/ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-3aaf35dd5e8f4bbd94ef8b44feecaefe
Quelldatensatz
uspto-grants-1995_06
Patentnummer
US05426119

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