반응 #347281

ord-e20ac178b2f740a5967ad3f1b2e57b9d

반응 방정식

Cc1ccc(C=O)cc1[N+](=O)[O-]
3-nitro-4-methylbenzaldehyde
COc1cc(CC#N)cc(OC)c1OC
3,4,5-trimethoxyphenylacetonitrile
[Na+].[OH-]
sodium hydroxide
COc1cc(/C(C#N)=C/c2ccc(C)c([N+](=O)[O-])c2)cc(OC)c1OC
intended compound
수율 14.1%
COc1cc(/C(C#N)=C/c2ccc(C)c([N+](=O)[O-])c2)cc(OC)c1OC
(Z)-3-(3-nitro-4-methylphenyl)-2-(3,4,5-trimethoxyphenyl)-prop-2-ene-nitrile
수율 14.1%

반응 조건

상세 조건
See reaction.notes.procedure_details.

후처리

  1. 1
    추출the mixture was extracted with dichloromethane three times
  2. 2
    건조dried over anhydrous sodium sulfate
  3. 3
    농축The organic layer was concentrated
  4. 4
    기타the residue was purified by silica gel column chromatography (dichloromethane)

실험 절차

5.0 g of 3-nitro-4-methylbenzaldehyde, 6.27 g of 3,4,5-trimethoxyphenylacetonitrile, 1.44 g of sodium hydroxide and 500 mg of trioctylmethylammonium chloride were dissolved in 25 ml of water and 500 ml of dichloromethane. The mixture was stirred vigorously for 3 hours at room temperature. The ice water was added to the mixture and the mixture was extracted with dichloromethane three times and dried over anhydrous sodium sulfate. The organic layer was concentrated and the residue was purified by silica gel column chromatography (dichloromethane) to give 1.5 g of the intended compound. The yield was 14.1%.

출처

DOI: 10.6084/m9.figshare.5104873.v1특허: US05525632uspto-grants-1996_06