Cyclohexene → Dimethyl bicyclo[4.1.0]heptane-7,7-dicarboxylate

HRID 487027

반응식

HRID 487027 반응식
[CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1.[N+](=[C:9]([C:14]([O:16][CH3:17])=[O:15])[C:10]([O:12][CH3:13])=[O:11])=[N-]>CC(CC(C)=O)=O.CC(CC(C)=O)=O.[Cu]>[CH:1]12[C:9]([C:14]([O:16][CH3:17])=[O:15])([C:10]([O:12][CH3:13])=[O:11])[CH:6]1[CH2:5][CH2:4][CH2:3][CH2:2]2

참가 물질

4

반응물 2

HCID 8079CyclohexeneHCID 5476732-Diazonio-1,3-dimethoxy-3-oxoprop-1-en-1-olate

생성물 1

HCID 283676Dimethyl bicyclo[4.1.0]heptane-7,7-dicarboxylate수율 57.1%

시약·촉매·용매 1

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

실험 절차

To stirred, refluxing mixture of 100.0 grams (1.22 mole) of cyclohexene and 0.037 gram (0.0001 mole) of cupric acetylacetonate was fed 22.7 grams (0.14 mole) of dimethyl diazomalonate over a 25-hour period by means of a syringe pump. Refluxing was continued for an additional 8 hours after which distillation of the reaction mixture was begun, employing a small Vigreux column. After removing about 32 grams of cyclohexene overhead, to a head temperature of 80° C., the residue was allowed to cool. The solidified residue was worked up by flash column chromatography on silica gel to give 17.53 grams (0.08 mole) of dimethyl bicyclo[4.1.0]heptane-7,7-dicarboxylate having a melting point of 83° C.-86° C. Elemental analysis of the product indicated the following:

후처리

  1. temperaturerefluxing
  2. customover a 25-hour
  3. temperatureRefluxing
  4. distillationafter which distillation of the reaction mixture
  5. customAfter removing about 32 grams of cyclohexene overhead
  6. customto a head temperature of 80° C.
  7. temperatureto cool

출처 및 근거

ORD 기록
ord-41a507e7428240fa944e791e4b034613
출처 데이터셋
uspto-grants-1994_03
특허 번호
US05292937

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