Water → HCID 10987988, Verbindung

HRID 1872093Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1872093
C([Li])CCC.[C:6]([CH:8]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[CH2:9]1)#[N:7].[C:16]1(=[O:22])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1.O>CCCCCC.O1CCCC1>[C:6]([C:8]1([C:16]2([OH:22])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[CH2:9]1)#[N:7]

Komponenten

7

Edukt 4

HCID 962WaterHCID 7967CyclohexanoneHCID 1388381-BenzocyclobutenecarbonitrileHCID 178418339Butyllithium

Produkt 1

HCID 10987988HCID 10987988, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8058HexaneLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

Whilst maintaining the temperature at -78° C., 69 ml of 1.6M butyllithium in n-hexane are added to a solution of 12.9 g of 1-cyanobenzocyclobutane in 200 ml of tetrahydrofuran. After stirring for half an hour at that temperature, 15.5 ml of cyclohexanone are added and the reaction mixture is brought back to room temperature. After stirring for 3 hours at room temperature, the reaction mixture is hydrolysed at -10° C. with water. After extraction with diethyl ether, the organic phase is washed with brine, dried over MgSO4 and concentrated in vacuo. The crystalline residue is recrystallised from isopropyl ether to yield 12.32 g of the desired product.

Aufarbeitung

  1. additionare added
  2. customis brought back to room temperature
  3. extractionAfter extraction with diethyl ether
  4. washthe organic phase is washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe crystalline residue is recrystallised from isopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-36fedf644c72436b8444abfa6eb68890
Quelldatensatz
uspto-grants-2000_08
Patentnummer
US06107345

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