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Diethyl Malonate → Ethyl 3-(2,4-dimethoxyphenyl)-2-ethoxycarbonyl-2-propenoate

HRID 1418169
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HRID 1418169 반응식
[CH3:1][O:2][C:3]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:4]=1[CH:5]=O.[C:13]([O:21][CH2:22][CH3:23])(=[O:20])[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16]>C1C=CC=CC=1.C(OCC)(=O)C.CCCCCC.C(O)(=O)C1C=CC=CC=1.N1CCCCC1>[CH3:1][O:2][C:3]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:4]=1[CH:5]=[C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:13]([O:21][CH2:22][CH3:23])=[O:20]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 2

HCID 7761Diethyl MalonateHCID 691752,4-Dimethoxybenzaldehyde

생성물 1

HCID 10757178Ethyl 3-(2,4-dimethoxyphenyl)-2-ethoxycarbonyl-2-propenoate수율 92.1%

시약·촉매·용매 5

HCID 243Benzoic Acid촉매HCID 8082Piperidine촉매HCID 241Benzene용매
HCID 8058Hexane용매
HCID 8857Ethyl Acetate용매

실험 절차

A solution of 10.0 g (60.2 mmol) of 2,4-dimethoxybenzaldehyde, 10.6 g (66.3 mmol) of diethyl malonate, 0.19 g (1.6 mmol) of benzoic acid and 0.20 ml (2.0 mmol) of piperidine in 43 ml of benzene was heated under reflux for 16 hours, whilst removing the water formed. At the end of this time, it was allowed to cool to room temperature, and then the reaction mixture was diluted with a 2:1 by volume mixture of ethyl acetate and hexane, and the diluted solution was washed with a saturated aqueous solution of sodium hydrogencarbonate, with 1N aqueous hydrochloric acid, with water and with a saturated aqueous solution of sodium chloride, in that order, after which it was dried. The solvent was removed by distillation under reduced pressure, and the resulting residue was recrystallized from a mixture of diisopropyl ether and hexane, to give 17.1 g (yield 92%) of the title compound as crystals, melting at 40°-41° C. (from a mixture of diisopropyl ether and hexane).

후처리

  1. temperatureunder reflux for 16 hours
  2. customwhilst removing the water
  3. customformed
  4. washthe diluted solution was washed with a saturated aqueous solution of sodium hydrogencarbonate, with 1N aqueous hydrochloric acid, with water and with a saturated aqueous solution of sodium chloride, in that order
  5. customafter which it was dried
  6. customThe solvent was removed by distillation under reduced pressure
  7. customthe resulting residue was recrystallized from a mixture of diisopropyl ether and hexane

출처 및 근거

ORD 기록
ord-ff35cc4490604c2bb0adaa27dd219b4c
출처 데이터셋
uspto-grants-1999_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05880147

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