Reaktion #361345

ord-eb5dc1724d7848e3850b97b42f2dc97f

Reaktionsgleichung

O
Water
CC(C)[CH2][AlH][CH2]C(C)C
DIBALH
CCCCCc1ccc(-c2ccc([C@H]3CC[C@H](C#N)CC3)cc2)cc1
4-(trans-4-cyanocyclohexyl)-4'-pentylbiphenyl
O=S(=O)(O)O
sulfuric acid
→
CCCCCc1ccc(-c2ccc([C@H]3CC[C@H](C=O)CC3)cc2)cc1
4-(trans-4-Formylcyclohexyl)-4'-pentylbiphenyl

Edukte

O
Water
—
solution
CC(C)[CH2][AlH][CH2]C(C)C
DIBALH
CCCCCc1ccc(-c2ccc([C@H]3CC[C@H](C#N)CC3)cc2)cc1
4-(trans-4-cyanocyclohexyl)-4'-pentylbiphenyl
O=S(=O)(O)O
sulfuric acid

Reagenzien

Keine

Lösungsmittel

CCCCCC
hexane
CCCCC
pentane

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigeThe organic phase is separated off
  2. 2
    Trocknendried over Na2SO4
  3. 3
    Sonstigeevaporated
  4. 4
    SonstigeColourless deliquescent crystals are obtained

Vorschrift

112 ml of a 20% solution of DIBALH in hexane are added dropwise to a solution of 33.2 g of 4-(trans-4-cyanocyclohexyl)-4'-pentylbiphenyl in 1 l of pentane, and the mixture is stirred for 18 hours. Water is then added dropwise until the evolution of gas subsides and then 200 ml of 25% sulfuric acid are added dropwise. The organic phase is separated off, dried over Na2SO4 and evaporated. Colourless deliquescent crystals are obtained.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05389292uspto-grants-1995_02