تفاعل #1005942

ord-02445459c6a74033bffeb3cffd807533

معادلة التفاعل

CO/N=C(\C=C(\C)COc1ccn(-c2ccc(Cl)cc2)n1)C(=O)OC
methyl(Z,2E)-5-[1-(4-chlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-4-methyl-pent-3-enoate
CN
methylamine
CNC(=O)C(C=C(C)COc1ccn(-c2ccc(Cl)cc2)n1)=NOC
5-[1-(4-chlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,4-dimethyl-pent-3-enamide

المذيبات

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    workup.WAITwas continued over night
  2. 2
    أخرىAfter removal of the solvent in vacuo the mixture
  3. 3
    أخرىwas purified by chromatography on silica with a heptane/ethyl acetate gradient
  4. 4
    أخرى90 mg of the desired Z-isomer have been collected

الإجراء التجريبي

0.68 g (1.87 mmol) methyl(Z,2E)-5-[1-(4-chlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-4-methyl-pent-3-enoate and E-isomer from the previous reaction have been dissolved in 3.0 ml THF. 2.0 ml 40% aqueous methylamine have been added at ambient temperature with stirring which was continued over night. After removal of the solvent in vacuo the mixture was purified by chromatography on silica with a heptane/ethyl acetate gradient. 90 mg of the desired Z-isomer have been collected. 1H-NMR (CDCl3): δ=2.03 (s); 2.85 (d); 3.97 (s); 4.64 (s); 5.87 (s); 6.02 (d); 6.65 (br); 7.35 (d); 7.50 (d); 7.67 (d).

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US09271501B2uspto-grants-2016_03