Potassium Hydroxide → 4-Ethynyl-5-methyl-3-phenyl-isoxazole

HRID 1984648Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1984648
CC(O)([C:4]#[C:5][C:6]1[C:7]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[N:8][O:9][C:10]=1[CH3:11])C.[OH-].[K+]>C1(C)C=CC=CC=1>[C:5]([C:6]1[C:7]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[N:8][O:9][C:10]=1[CH3:11])#[CH:4]

Komponenten

4

Edukt 2

HCID 14797Potassium HydroxideHCID 688532502-Methyl-4-(5-methyl-3-phenyl-isoxazol-4-yl)-but-3-yn-2-ol

Produkt 1

HCID 534346474-Ethynyl-5-methyl-3-phenyl-isoxazoleAusbeute 87,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

To a solution of 2-methyl-4-(5-methyl-3-phenyl-isoxazol-4-yl)-but-3-yn-2-ol (3.77 g, 15.6 mmol) in toluene (38 mL) was added potassium hydroxide (350 mg, 6.24 mmol) and the reaction mixture was stirred for 1.25 h at 110° C. before being cooled to ambient temperature and separated between ethyl acetate (500 mL) and aqueous ammonium chloride (1 M, 400 mL). The aqueous layer was extracted with ethyl acetate (500 mL) and the combined organic layers were dried over sodium sulfate and concentrated. Purification by chromatography (SiO2, heptane:ethyl acetate=100:0 to 90:10) afforded the title compound (2.50 g, 87%) as a yellow solid. MS: m/e=184.1 [M+H]+.

Aufarbeitung

  1. temperaturebefore being cooled to ambient temperature
  2. customseparated between ethyl acetate (500 mL) and aqueous ammonium chloride (1 M, 400 mL)
  3. extractionThe aqueous layer was extracted with ethyl acetate (500 mL)
  4. dry with materialthe combined organic layers were dried over sodium sulfate
  5. concentrationconcentrated
  6. customPurification by chromatography (SiO2, heptane:ethyl acetate=100:0 to 90:10)

Quellen und Nachweise

ORD-Eintrag
ord-de654f70bf6f4a2fbfbfaf9d4bd77bbb
Quelldatensatz
uspto-grants-2009_06
Patentnummer
US07544704B2

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