alpha-Ethynylbenzenemethanol → Ethyl 5-(hydroxy(phenyl)methyl)isoxazole-3-carboxylate

HRID 1918612

Reaktionsgleichung

Reaktionsgleichung von HRID 1918612
[C:1]1([CH:7]([OH:10])[C:8]#[CH:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl/[C:12](=[N:18]\[OH:19])/[C:13]([O:15][CH2:16][CH3:17])=[O:14].C(=O)([O-])O.[Na+]>C(OCC)(=O)C.O>[OH:10][CH:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[C:8]1[O:19][N:18]=[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:9]=1

Komponenten

6

Edukt 3

HCID 20155alpha-EthynylbenzenemethanolHCID 516892Sodium BicarbonateHCID 95760052-Chloro-2-hydroxyiminoacetic acid ethyl ester

Produkt 1

HCID 66831982Ethyl 5-(hydroxy(phenyl)methyl)isoxazole-3-carboxylateAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

1-phenylprop-2-yn-1-ol (0.802 mL, 6.60 mmol) was added to a mixture of (Z)-ethyl 2-chloro-2-(hydroxyimino)acetate (0.50 g; 3.30 mmol) and sodium hydrogen carbonate (0.554 g; 6.60 mmol) in ethyl acetate (15 mL) and water (0.2 mL) and stirred at room temperature for 24 hours. The resulting mixture was filtered and concentrated under reduced pressure. The crude mixture was purified by flash chromatography on silica (eluent 2 to 40% ethyl acetate in heptane) to yield 0.571 g (70%) of ethyl 5-(hydroxy(phenyl)methyl)isoxazole-3-carboxylate as a colorless oil.

Aufarbeitung

  1. filtrationThe resulting mixture was filtered
  2. concentrationconcentrated under reduced pressure
  3. customThe crude mixture was purified by flash chromatography on silica (eluent 2 to 40% ethyl acetate in heptane)

Quellen und Nachweise

ORD-Eintrag
ord-b37555085a0f42bbb0838341fda5dbf3
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08618138B2

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