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

HRID 77535

Reaktionsgleichung

Reaktionsgleichung von HRID 77535
[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]

Komponenten

5

Edukt 3

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

Produkt 1

HCID 86684675(Z)-methyl 3-(2,4-dimethoxyphenyl)-3-((2-hydroxyethyl)amino)acrylateAusbeute 65,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Reaktionsbedingungen

Temperatur
83 °C

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-87dbaacf1b86412eb9a8aea123b1f8b3
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08841314B2

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