Reaction #1857547

ord-a0f60c01467e4bb49e4d352d2ae3b07f

Reaction equation

ClCCl
dichloro methane
[H-].[Na+]
sodium hydride
C=CC(O)(Cn1cncn1)c1ccc(Oc2ccc(Cl)cc2)cc1Cl
2-[2-chloro-4-(4-chlorophenoxy)phenyl]-1-(1,2,4-triazol-1-yl)but-3-en-2-ol
CI
methyl iodide
C=CC(Cn1cncn1)(OC)c1ccc(Oc2ccc(Cl)cc2)cc1Cl
desired compound
C=CC(Cn1cncn1)(OC)c1ccc(Oc2ccc(Cl)cc2)cc1Cl
1-[2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-methoxy-but-3-enyl]-1,2,4-triazole

Solvents

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    TemperatureThe mixture was then heated for 10 h
  2. 2
    Temperatureto reflux
  3. 3
    Otherthe organic phase was dried
  4. 4
    Otherevaporated
  5. 5
    Otherto obtain the crude product
  6. 6
    OtherThis was purified by column chromatography

Procedure

2-[2-chloro-4-(4-chlorophenoxy)phenyl]-1-(1,2,4-triazol-1-yl)but-3-en-2-ol (0.4 g) was dissolved in THF (10 mL) and sodium hydride (0.03 g) was added. The mixture was stirred for 30 min at room temperature and methyl iodide (0.08 mL) was added. The mixture was then heated for 10 h to reflux. Brine and dichloro methane were added, the organic phase was dried and evaporated to obtain the crude product. This was purified by column chromatography to obtain 0.04 g of the desired compound.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US09247747B2uspto-grants-2016_02