Diphenylacetylene → 1,1-Dimethyl 2,3-diphenyl-2-cyclopropene-1,1-dicarboxylate

HRID 487022

반응식

HRID 487022 반응식
[C:1]1([C:7]#[C:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N+](=[C:17]([C:22]([O:24][CH3:25])=[O:23])[C:18]([O:20][CH3:21])=[O:19])=[N-]>CC(CC(C)=O)=O.CC(CC(C)=O)=O.[Cu]>[C:1]1([C:7]2[C:17]([C:22]([O:24][CH3:25])=[O:23])([C:18]([O:20][CH3:21])=[O:19])[C:8]=2[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

참가 물질

4

반응물 2

HCID 10390DiphenylacetyleneHCID 5476732-Diazonio-1,3-dimethoxy-3-oxoprop-1-en-1-olate2회

생성물 1

HCID 128090341,1-Dimethyl 2,3-diphenyl-2-cyclopropene-1,1-dicarboxylate수율 26.8%

시약·촉매·용매 1

HCID 45052134Bis(pentane-2,4-dione-kappa~2~O~2~,O~4~)copper촉매

반응 조건

온도
120 °C

실험 절차

A 100 millilater round-bottom flask was equipped with a magnetic stirrer and reflux condenser with N2 inlet. The flask was charged with 25.0 grams (0.140 mole) of diphenylacetylene and 140 milligrams of cupric acetylacetonate. The mixture was heated to 120° C. using an oil bath and 8.85 grams (0.056 mole) of dimethyl diazomalonate was added over 24 hours using a syringe pump. When all of the dimethyl diazomalonate had been added, heating at 120° C. was continued for 8 hours. The diphenylacetylene was distilled off under vacuum, boiling point 170° C./19 Mm. The residue was purified by flash chromatography eluting with 75:25 hexane-ethyl acetate to give 4.65 grams (0.015 mole) of the desired product as a white solid. NMR analysis of the product indicated the following:

후처리

  1. customA 100 millilater round-bottom flask was equipped with a magnetic stirrer
  2. temperaturereflux condenser with N2 inlet
  3. temperatureheating at 120° C.
  4. distillationThe diphenylacetylene was distilled off under vacuum, boiling point 170° C./19 Mm
  5. customThe residue was purified by flash chromatography
  6. washeluting with 75:25 hexane-ethyl acetate

출처 및 근거

ORD 기록
ord-66d65d320ac04264a52aa06affbf25cc
출처 데이터셋
uspto-grants-1994_03
특허 번호
US05292937

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