Acetic Acid → (Z)-methyl 3-(2,4-dimethoxyphenyl)-3-((2-hydroxyethyl)amino)acrylate

HRID 77535ノート

反応式

HRID 77535 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[C:11](=O)[CH2:12][C:13]([O:15][CH3:16])=[O:14].C(O)(=O)C.[CH2:22]([CH2:24][NH2:25])[OH:23]>CC(O)C>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1/[C:11](/[NH:25][CH2:24][CH2:22][OH:23])=[CH:12]/[C:13]([O:15][CH3:16])=[O:14]

参加物

5

反応物 3

HCID 176Acetic AcidHCID 700Ethanolamine2 回HCID 2063901Methyl 2,4-dimethoxy-beta-oxobenzenepropanoate

生成物 1

HCID 86684675(Z)-methyl 3-(2,4-dimethoxyphenyl)-3-((2-hydroxyethyl)amino)acrylate収率 65.8%

試薬・触媒・溶媒 1

HCID 3776Isopropanol溶媒

反応条件

温度
83 °C

実験手順

To a mixture of methyl 3-(2,4-dimethoxyphenyl)-3-oxopropanoate (3.50 g, 14.69 mmol) and acetic acid (0.17 mL, 2.94 mmol) in i-PrOH (70 mL) was added ethanolamine (0.88 mL, 14.69 mmol) and the reaction mixture was heated to 83° C. Additional ethanolamine (0.88 mL, 14.69 mmol) was added to the reaction mixture at two, four and six hours. After stirring at 80° C. for 48 hours, the reaction mixture was cooled and concentrated under reduced pressure before the residue was suspended in equal parts of a saturated sodium bicarbonate solution and water under N2. After stirring overnight, the solids were collected by vacuum filtration and dried in a vacuum oven at 30° C. overnight to afford the title compound (2.72 g, 63%) as a beige colored power.

後処理

  1. temperaturethe reaction mixture was cooled
  2. concentrationconcentrated under reduced pressure before the residue
  3. stirringAfter stirring overnight
  4. filtrationthe solids were collected by vacuum filtration
  5. customdried in a vacuum oven at 30° C. overnight

出典と根拠

ORDレコード
ord-87dbaacf1b86412eb9a8aea123b1f8b3
出典データセット
uspto-grants-2014_09
特許番号
US08841314B2

反応ノート

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