Hydrochloric Acid → (Z)-3-(7-methoxy-4-methyloxycarbonylbenzo[b]furan-2-yl)-2-propenoic acid

HRID 1091835Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1091835
[CH3:1][O:2][C:3]([C:5]1[C:13]2[CH:12]=[C:11]([CH:14]=O)[O:10][C:9]=2[C:8]([O:16][CH3:17])=[CH:7][CH:6]=1)=[O:4].C(O)(=O)[CH2:19][C:20]([OH:22])=[O:21].N1CCCCC1.Cl>C1(C)C=CC=CC=1>[CH3:17][O:16][C:8]1[C:9]2[O:10][C:11](/[CH:14]=[CH:19]\[C:20]([OH:22])=[O:21])=[CH:12][C:13]=2[C:5]([C:3]([O:2][CH3:1])=[O:4])=[CH:6][CH:7]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 867Malonic AcidHCID 8082PiperidineHCID 86636828Methyl-2-formyl-7-methoxybenzo[b]furan-4-carboxylate

Produkt 1

HCID 66592575(Z)-3-(7-methoxy-4-methyloxycarbonylbenzo[b]furan-2-yl)-2-propenoic acidAusbeute 76,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a well stirred solution of Methyl-2-formyl-7-methoxybenzo[b]furan-4-carboxylate (from step 7) (2.0 g, 8.53 mmol) in toluene (50.0 mL) was added malonic acid (1.33 g, 12.80 mmol) and Piperidine (0.5 ml). The reaction mixture was then refluxed for 3-4 hours. Reaction mixture was cooled to room temperature, acidified with 10% aqueous HCl solution and extracted with ethyl acetate (2×100 mL). The combined organic layers were washed with water (2×100 mL0 and dried over anhydrous sodium sulfate. Removal of solvent under vacuo gave product (1.8 g) as light yellow solid.

Aufarbeitung

  1. temperatureThe reaction mixture was then refluxed for 3-4 hours
  2. customReaction mixture
  3. extractionextracted with ethyl acetate (2×100 mL)
  4. washThe combined organic layers were washed with water (2×100 mL0
  5. dry with materialdried over anhydrous sodium sulfate
  6. customRemoval of solvent under vacuo

Quellen und Nachweise

ORD-Eintrag
ord-285f6e1d9fdc44d296e8c958c1814831
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08129401B2

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