Diethyl methylmalonate → 2-[(2Z)-3-Chloro-2-butenyl]-2-methylmalonic Acid Diethyl Ester

HRID 543514

반응식

HRID 543514 반응식
[Na].[CH3:2][CH:3]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[C:4]([O:6][CH2:7][CH3:8])=[O:5].Cl[CH2:15][CH:16]=[C:17]([Cl:19])[CH3:18]>C(O)C>[CH2:12]([O:11][C:9](=[O:10])[C:3]([CH2:15]/[CH:16]=[C:17](\[Cl:19])/[CH3:18])([CH3:2])[C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH3:13]

참가 물질

5

반응물 3

HCID 11857Diethyl methylmalonateHCID 135561,3-Dichloro-2-buteneHCID 5360545Sodium

생성물 1

HCID 132164822-[(2Z)-3-Chloro-2-butenyl]-2-methylmalonic Acid Diethyl Ester

시약·촉매·용매 1

HCID 702Ethanol용매

반응 조건

온도
75 °C

실험 절차

11.5 g of sodium cut into small pieces was introduced into a three-necked flask equipped with agitator, reflux condenser, and dropping funnel. To this charge was added dropwise 250 ml of absolute ethanol so quickly that the solution was boiling vigorously. Then 87 g of distilled diethyl methylmalonate was added dropwise to the hot alcoholate solution. After allowing the mixture to cool to about 75° C., the reaction solution was combined with 66 g of 1,3-dichloro-2-butene dropwise; the solution turned yellow during this step. After 2 hours of agitation under heating, the suspension, at this point having pH 5-6 and being almost completely decolorized, was freed of precipitated sodium chloride by filtration. The filtrate was concentrated and combined with the methylene chloride obtained by washing the precipitate. The organic solution was thereafter shaken with saturated sodium chloride solution, dried over magnesium sulfate, concentrated on a forced circulation evaporator, and fractionated under vacuum. Yield: 105 g of the desired diester, bp2.5 110° C.

후처리

  1. additionwas introduced into a three-necked flask
  2. customequipped with agitator
  3. temperaturereflux condenser
  4. temperatureAfter 2 hours of agitation under heating
  5. filtrationwas freed of precipitated sodium chloride by filtration
  6. concentrationThe filtrate was concentrated
  7. customobtained
  8. washby washing the precipitate
  9. dry with materialdried over magnesium sulfate
  10. concentrationconcentrated on a forced circulation evaporator
  11. customYield: 105 g of the desired diester, bp2.5 110° C.

출처 및 근거

ORD 기록
ord-57a1c803e7c448e0b3d4d7becedad265
출처 데이터셋
uspto-grants-1984_05
특허 번호
US04446147

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