Potassium Hydroxide → Diisopropyl 2-vinylcyclopropane-1,1-dicarboxylate

HRID 1413988

반응식

HRID 1413988 반응식
C(C1CC1)=C.[CH2:6](Cl)/[CH:7]=[CH:8]/[CH2:9]Cl.[C:12]([O:21][CH:22]([CH3:24])[CH3:23])(=[O:20])[CH2:13][C:14]([O:16][CH:17]([CH3:19])[CH3:18])=[O:15].[Cl-].C(C([NH3+])(C(=O)CCCCCCC)C(=O)CCCCCCC)(=O)CCCCCCC.[OH-].[K+]>O>[CH:7]([CH:8]1[CH2:9][C:13]1([C:14]([O:16][CH:17]([CH3:19])[CH3:18])=[O:15])[C:12]([O:21][CH:22]([CH3:24])[CH3:23])=[O:20])=[CH2:6]

참가 물질

7

반응물 5

HCID 14797Potassium HydroxideHCID 83223Diisopropyl malonateHCID 136498EthenylcyclopropaneHCID 6421971,4-Dichloro-2-butene, (2E)-HCID 77620884Tricaprylylmethyl ammonium chloride

생성물 1

HCID 13137099Diisopropyl 2-vinylcyclopropane-1,1-dicarboxylate수율 153.1%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

To illustrate the preparation of vinylcyclopropane derivatives via malonic ester condensation in an aqueous medium, the following experiment was conducted: To a flask provided with a stirrer and containing 125 g (1.0 mol) trans 1,4-dichlorobutene-2, 94 g (0.50 mol) diisopropyl malonate and 3.2 g (1.63 mol percent based on the malonate ester) tricaprylylmethylammonium chloride were added dropwise over a 30-minute perid with vigorous stirring 168 g 50% aqueous potassium hydroxide solution. Cooling was provided to maintain the reaction temperature at 25°-30° C. After five hours the reaction mixture was poured into water and extracted three times with ethyl ether. The combined etheral layers were dried over magnesium sulfate, filtered and concentrated to afford 184 g (67.2% yield) diisopropyl 2-vinylcyclopropane-1,1-dicarboxylate. Bp 77°-78° C.(0.5 mm); nD24° 1.4482. Infrared and proton nmr spectra were consistent with the desired structure. Similar results were obtained using other quaternary ammonium compounds, however, when the onium compound was omitted the reaction did not proceed.

후처리

  1. customTo a flask provided with a stirrer
  2. additionwere added dropwise over a 30-minute perid
  3. temperatureCooling
  4. customwas provided
  5. temperatureto maintain the reaction temperature at 25°-30° C
  6. extractionextracted three times with ethyl ether
  7. dry with materialThe combined etheral layers were dried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated

출처 및 근거

ORD 기록
ord-a28b7e9d3c8e42619d832a75bdd71ed9
출처 데이터셋
uspto-grants-1981_02
특허 번호
US04252739

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