Acetic Acid → HCID 10679379, Verbindung

HRID 1087021Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1087021
[O:1]1[CH2:6][CH2:5][C:4](=O)[CH2:3][CH2:2]1.[C:8]([CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])#[N:9].C([O-])(=O)C.[NH4+].C(O)(=O)C>C1(C)C=CC=CC=1>[CH2:14]([O:13][C:11]([C:10]([C:8]#[N:9])=[C:4]1[CH2:5][CH2:6][O:1][CH2:2][CH2:3]1)=[O:12])[CH3:15]

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 7764Ethyl cyanoacetateHCID 121599Tetrahydro-4H-pyran-4-oneHCID 517165Ammonium Acetate

Produkt 1

HCID 10679379HCID 10679379, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel2×

Versuchsvorschrift

A mixture of tetrahydropyran-4-one (12 g), ethyl cyanoacetate (13.6 g), ammonium acetate (1.2 g), glacial acetic acid (2.4 ml) and toluene (15 ml) is stirred at reflux for 16 hours. The mixture is diluted with toluene and the organic layer is separated, washed with water, then brine, and dried over magnesium sulfate. It is concentrated at reduced pressure to an oil which solidifies. It is further purified by flash chromatography through silica gel with methylene chloride as eluent. The desired fractions are combined and concentrated to dryness at reduced pressure to afford 4-(alpha-ethoxycarbonyl-cyanomethylene)-tetrahydropyran.

Aufarbeitung

  1. temperatureat reflux for 16 hours
  2. customthe organic layer is separated
  3. washwashed with water
  4. dry with materialbrine, and dried over magnesium sulfate
  5. concentrationIt is concentrated at reduced pressure to an oil which
  6. customIt is further purified by flash chromatography through silica gel with methylene chloride as eluent
  7. concentrationconcentrated to dryness at reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-6479001f778e4d92849c58b9dfc4ba4b
Quelldatensatz
uspto-grants-1991_07
Patentnummer
US05034381

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