Reaktion #64195

ord-fbb1f373f49f4069a88ae022b4f78436

Reaktionsgleichung

O=C1CCCCCC1
cycloheptanone
CC(C)[N-]C(C)C.[Li+]
lithium diisopropylamide
N#Cc1ccc(Cc2nc[nH]n2)cc1
4-[1-(1,2,4-triazolyl)methyl]benzonitrile
O
water
N#Cc1ccc(C(c2nc[nH]n2)C2(O)CCCCCC2)cc1
4-[1-hydroxycyclohept-1-yl-1-(1,2,4-triazolyl) methyl]benzonitrile
Ausbeute 98.2%

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Temperaturheated to 25°
  2. 2
    Extraktionextracted twice with ethyl acetate
  3. 3
    Waschenwashed neutral with water
  4. 4
    Trocknendried over sodium sulfate
  5. 5
    Einengenconcentrated to dryness under vacuum

Vorschrift

5 g of 4-[1-(1,2,4-triazolyl)methyl]benzonitrile is dissolved in 100 ml of tetrahydrofuran and combined at -50° with 19.8 ml of 1.5-molar solution of lithium diisopropylamide in tetrahydrofuran, stirred for 0.5 hour, further stirred for 1 hour at -70° with 3.05 g of cycloheptanone, and heated to 25°. Then the mixture is combined with water, extracted twice with ethyl acetate, washed neutral with water, dried over sodium sulfate, and concentrated to dryness under vacuum, thus obtaining 7.9 g of crude 4-[1-hydroxycyclohept-1-yl-1-(1,2,4-triazolyl) methyl]benzonitrile.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05411982uspto-grants-1995_05