m-Trifluoromethylphenylacetonitrile → 2-Thien-2-yl-3-oxo-4-(3-trifluoromethylphenyl)-5-amino-2,3-dihydrofuran

HRID 485616

Reaktionsgleichung

Reaktionsgleichung von HRID 485616
[Na].[O-]CC.[Na+].[S:6]1[CH:10]=[CH:9][CH:8]=[C:7]1[CH:11]([OH:16])[C:12]([O:14]C)=O.[F:17][C:18]([F:29])([F:28])[C:19]1[CH:20]=[C:21]([CH2:25][C:26]#[N:27])[CH:22]=[CH:23][CH:24]=1>C(O)C.O>[S:6]1[CH:10]=[CH:9][CH:8]=[C:7]1[CH:11]1[C:12](=[O:14])[C:25]([C:21]2[CH:22]=[CH:23][CH:24]=[C:19]([C:18]([F:28])([F:17])[F:29])[CH:20]=2)=[C:26]([NH2:27])[O:16]1

Komponenten

7

Edukt 4

HCID 75360m-TrifluoromethylphenylacetonitrileHCID 2723922Sodium ethoxideHCID 5360545SodiumHCID 13682356Methyl thien-2-yl-hydroxyacetate

Produkt 1

HCID 136911642-Thien-2-yl-3-oxo-4-(3-trifluoromethylphenyl)-5-amino-2,3-dihydrofuranAusbeute 12,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittel2×HCID 962WaterLösungsmittel

Versuchsvorschrift

A dry, 250-ml, three-neck, round-bottom flask equipped with a mechanical stirrer, addition funnel and a reflux condenser bearing a nitrogen inlet tube was charged with 4.2 g of sodium and 100 ml of absolute ethanol. To the resulting sodium ethoxide solution was added dropwise a mixture of 21.1 g of methyl thien-2-yl-hydroxyacetate and 22.7 g of m-trifluoromethylphenyl-acetonitrile in 20 ml of ethanol. The resulting mixture was heated at reflux for 4-5 hours after which time it was added to 300-400 ml of water and extracted with petroleum ether. The aqueous phase was acidified with aqueous 10 weight percent hydrochloric acid and extracted two times with diethyl ether. The ether extracts were washed twice with saturated aqueous sodium bicarbonate, dried over magnesium sulfate and concentrated in vacuo to yield a thick dark oil. This oil was triturated with 20-30% ether/petroleum ether which afforded 4.9 g of the title compound as a tan powder.

Aufarbeitung

  1. customA dry, 250-ml, three-neck, round-bottom flask equipped with a mechanical stirrer, addition funnel and a reflux condenser
  2. temperatureThe resulting mixture was heated
  3. temperatureat reflux for 4-5 hours after which time it
  4. extractionextracted with petroleum ether
  5. extractionextracted two times with diethyl ether
  6. washThe ether extracts were washed twice with saturated aqueous sodium bicarbonate
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated in vacuo
  9. customto yield a thick dark oil
  10. customThis oil was triturated with 20-30% ether/petroleum ether which

Quellen und Nachweise

ORD-Eintrag
ord-fee1c62f64834886b18149b90549224d
Quelldatensatz
uspto-grants-1985_08
Patentnummer
US04537623

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