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

HRID 1418169
ノート
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反応式

HRID 1418169 の反応式
[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]
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 2

HCID 7761Diethyl MalonateHCID 691752,4-Dimethoxybenzaldehyde

生成物 1

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

試薬・触媒・溶媒 5

HCID 243Benzoic Acid触媒HCID 8082Piperidine触媒HCID 241Benzene溶媒
HCID 8058Hexane溶媒
HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-ff35cc4490604c2bb0adaa27dd219b4c
出典データセット
uspto-grants-1999_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05880147

反応ノート

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