Water → Methyl 4-acetamido-3-methoxycinnamate

HRID 1699164Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1699164
[C:1]([NH:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]=O)=[CH:7][C:6]=1[O:13][CH3:14])(=[O:3])[CH3:2].C1(P(=[CH:34][C:35]([O:37][CH3:38])=[O:36])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>O1CCCC1>[C:1]([NH:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]=[CH:34][C:35]([O:37][CH3:38])=[O:36])=[CH:7][C:6]=1[O:13][CH3:14])(=[O:3])[CH3:2]

Komponenten

5

Edukt 3

HCID 962WaterHCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 183218014-Acetamido-3-methoxybenzaldehyde

Produkt 1

HCID 54551695Methyl 4-acetamido-3-methoxycinnamateAusbeute 22,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 4-acetamido-3-methoxybenzaldehyde (388 mg) in tetrahydrofuran (10 ml) was added methyl (triphenylphosphoranylidene)acetate (739 mg), and the mixture was stirred for 2 hours at ambient temperature. The mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with water and brine, dried over magnesium sulfate and concentrated in vacuo. The residue was purified by column chromatography on silica gel (chloroform:methanol=30:1, V/V) to give methyl 4-acetamido-3-methoxycinnamate (113 mg).

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography on silica gel (chloroform:methanol=30:1, V/V)

Quellen und Nachweise

ORD-Eintrag
ord-63abb9f3c42846f49d0b27dfc0cdb336
Quelldatensatz
uspto-grants-2002_02
Patentnummer
US06344462B1

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