Malonic Acid → 3-Thiophen-2-ylprop-2-enoic acid

HRID 460360

Reaktionsgleichung

Reaktionsgleichung von HRID 460360
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]=O.C(O)(=O)[CH2:9][C:10]([OH:12])=[O:11].C([O-])(=O)C.[NH4+]>CN(C=O)C.C(OCC)(=O)C>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]=[CH:9][C:10]([OH:12])=[O:11]

Komponenten

6

Edukt 3

HCID 867Malonic AcidHCID 73642-Thiophenecarboxaldehyde2×HCID 517165Ammonium Acetate

Produkt 1

HCID 928683-Thiophen-2-ylprop-2-enoic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of thiophene-2-carbaldehyde (Compound 66a) (1.20 g, 0.0107 mol), malonic acid (1.11 g, 0.0107 mol) and ammonium acetate (0.825 g, 0.0107 mol) in DMF (8.5 mL) was heated to 100° C. for 3 h. The system was diluted with ethyl acetate and washed with water and dried over MgSO4. The solvent was removed in vacuo and the title compound was purified by silica gel column chromatography using 3:1 Hexanes:ethyl acetate as the eluent.

Aufarbeitung

  1. washwashed with water
  2. dry with materialdried over MgSO4
  3. customThe solvent was removed in vacuo
  4. customthe title compound was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-dc6b503372ff491c9ba7d69950f12636
Quelldatensatz
uspto-grants-2007_03
Patentnummer
US07196110B2

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