Acetic Acid → HCID 89488364, Verbindung

HRID 570131

Reaktionsgleichung

Reaktionsgleichung von HRID 570131
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:12]=[C:11]([O:13][CH2:14][C:15]([CH3:17])=O)[NH:10][N:9]=2)=[CH:4][CH:3]=1.C(O)(=O)C.CC1C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1.CCOC(C)=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:12]=[C:11]3[O:13][CH:14]=[C:15]([CH3:17])[N:10]3[N:9]=2)=[CH:4][CH:3]=1

Komponenten

6

Edukt 3

HCID 176Acetic AcidHCID 6101p-Toluenesulfonic acidHCID 178468630HCID 178468630, Verbindung

Produkt 1

HCID 89488364HCID 89488364, VerbindungAusbeute 46,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

To a stirred solution of 1-{[3-(4-fluorophenyl)-1H-pyrazol-5-yl]oxy}acetone (0.25 g, 1.0 mmol) in toluene, equipped with dean stark apparatus, acetic acid (2 ml) and p-TsOH (25 mg, cat.) was charged at RT and the reaction mass was refluxed at 130° C. for 16 h. After completion, the reaction was diluted with EtOAc (50 ml) and washed with brine. The organic layer dried over sodium sulphate and concentrated under reduced pressure to get the crude which was then purified by column chromatography 100-200 mesh) eluted with 5-10% ethyl acetate in hexane as eluent to get compound 6-(4-fluorophenyl)-3-methylpyrazolo[5,1-b][1,3]oxazole (0.1 g, yield 43%).

Aufarbeitung

  1. additionwas charged at RT
  2. washwashed with brine
  3. dry with materialThe organic layer dried over sodium sulphate
  4. concentrationconcentrated under reduced pressure
  5. customto get the crude which
  6. customwas then purified by column chromatography 100-200 mesh)
  7. washeluted with 5-10% ethyl acetate in hexane as eluent

Quellen und Nachweise

ORD-Eintrag
ord-3c0b78a0836c4cfebba1d3ef6e030625
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09023844B2

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