Реакция #40717

ord-7a8b9422f4634db6947a7b29d86ba228

Уравнение реакции

COc1cc(OC)c(N=[N+]=[N-])cc1Cl
1-Azido-5-chloro-2,4-dimethoxy-benzene
COC(=O)CC(=O)c1ccc(F)cc1
3-(4-Fluoro-phenyl)-3-oxo-propionic acid methyl ester
CC[O-].[Na+]
sodium ethoxide
COc1cc(OC)c(-n2nnc(C(=O)O)c2-c2ccc(F)cc2)cc1Cl
1-(5-Chloro-2,4-dimethoxy-phenyl)-5-(4-fluoro-phenyl)-1H-[1,2,3]triazole-4-carboxylic acid

Растворители

Условия реакции

Подробные условия
See reaction.notes.procedure_details.

Обработка

  1. 1
    ДругоеDuring the reaction
  2. 2
    ДругоеAfter that, EtOH was evaporated off
  3. 3
    Другоеthe resulting oil was dried in vacuum
  4. 4
    ДругоеTrituration with ether (15 mL) gave light brown solids, which
  5. 5
    Другоеwere removed by filtration
  6. 6
    Промывкаwashed with ether
  7. 7
    workup.DISSOLUTIONThe solids then re-dissolved in CHCl3
  8. 8
    Фильтрацияfiltered
  9. 9
    ДругоеAfter evaporation of the solvent
  10. 10
    Другоеlight brown solids were obtained (0.35 g, 50%)

Методика

1-Azido-5-chloro-2,4-dimethoxy-benzene (0.4 g, 1.9 mmol), 3-(4-Fluoro-phenyl)-3-oxo-propionic acid methyl ester (0.42 g, 2.2 mmol) and sodium ethoxide in EtOH (70 mg of sodium in 15 mL EtOH) were refluxed for 3 hours. During the reaction, the solution turned brown from dark green. After that, EtOH was evaporated off and the resulting oil was dried in vacuum. Trituration with ether (15 mL) gave light brown solids, which were removed by filtration and washed with ether. The solids then re-dissolved in CHCl3 and filtered. After evaporation of the solvent, light brown solids were obtained (0.35 g, 50%).

Источник

DOI: 10.6084/m9.figshare.5104873.v1Патент: US07728016B2uspto-grants-2010_06