Water → cis-Diethyl cyclopropane-1,2-dicarboxylate

HRID 1940479

반응식

HRID 1940479 반응식
[H-].[Na+].[C:3]([O:7][CH2:8][CH3:9])(=[O:6])[CH:4]=[CH2:5].Cl[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13].O>C1(C)C=CC=CC=1.C(O)C>[C@@H:4]1([C:3]([O:7][CH2:8][CH3:9])=[O:6])[CH2:5][C@@H:11]1[C:12]([O:14][CH2:15][CH3:16])=[O:13]

참가 물질

7

반응물 4

HCID 962WaterHCID 7751Ethyl chloroacetateHCID 8821Ethyl AcrylateHCID 24758Sodium hydride

생성물 1

HCID 642980cis-Diethyl cyclopropane-1,2-dicarboxylate수율 35.1%

시약·촉매·용매 2

HCID 702Ethanol촉매HCID 1140Toluene용매

실험 절차

To a stirred suspension of 32.8 g (818.8 mmol) of 60% sodium hydride mineral oil dispersion in 200 mL of toluene under nitrogen, was added between 10 to 20 mL of a blend of ethyl acrylate (81.2 g, 810.7 mmol) and ethyl chloroacetate (99.4 g, 810.7 mmol) followed by several drops of ethanol. After an induction period of about 1 h, steady gas and heat evolution began with the reaction mixture temperature reaching 35° C. The remaining mixed ester reagent was carefully added dropwise with ice-bath cooling so as to maintain a reaction temperature of 30°-80° C. After the addition was complete (4 h), the mixture was cooled to room temperature and carefully poured into water (300 mL). The organic layer was separated and dried (MgSO4) and evaporated to a dry residue. The dry residue was chromatographed on silica gel using 10% ethyl acetate in hexane as the eluant. The fractions containing the desired compound were combined and evaporated to dryness under reduced pressure to give 53.0 g of the title compound of Step A as a clear oil (35% yield). IR (neat, cm-1): 1728.9 (C=O);

후처리

  1. temperatureAfter an induction period of about 1 h, steady gas and heat evolution
  2. customreaching 35° C
  3. additionwas carefully added dropwise with ice-bath
  4. temperaturecooling so as
  5. temperatureto maintain a reaction temperature of 30°-80° C
  6. additionAfter the addition
  7. custom(4 h)
  8. customThe organic layer was separated
  9. dry with materialdried (MgSO4)
  10. customevaporated to a dry residue
  11. customThe dry residue was chromatographed on silica gel using 10% ethyl acetate in hexane as the eluant
  12. additionThe fractions containing the desired compound
  13. customevaporated to dryness under reduced pressure

출처 및 근거

ORD 기록
ord-a836381f850d4c8f84c72e374f10fded
출처 데이터셋
uspto-grants-1997_12
특허 번호
US05700761

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