Hydrochloric Acid → HCID 23079541, Verbindung

HRID 1365047Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1365047
[CH2:1]([O:8][C:9]1[C:13]([C:14](O)=[O:15])=[C:12]([Br:17])[N:11]([CH:18]([CH3:20])[CH3:19])[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.Cl>O1CCCC1>[CH2:1]([O:8][C:9]1[C:13]([CH2:14][OH:15])=[C:12]([Br:17])[N:11]([CH:18]([CH3:20])[CH3:19])[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 230795363-Benzyloxy-5-bromo-1-isopropylpyrazole-4-carboxylic acid

Produkt 1

HCID 23079541HCID 23079541, VerbindungAusbeute 68 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

3-Benzyloxy-5-bromo-1-isopropylpyrazole-4-carboxylic acid (4.6 g) was dissolved in tetrahydrofuran (30 mL), and borane-tetrahydrofuran complex, 1M tetrahydrofuran solution (21 mL) was delivered by drops into the stirred solution under ice cooling. The mixture was stirred at room temperature for 1 hour. The reaction mixture was cooled with ice bath, and water (50 mL) was delivered by drops into the mixture. Hydrochloric acid (1 mol/L, 20 mL) was delivered by drops into the mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the obtained residue was purified by column chromatography on silica gel (eluent: ethyl acetate/hexane=1/5) to give the title compound (3.0 g).

Aufarbeitung

  1. temperatureThe reaction mixture was cooled with ice bath
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was removed under reduced pressure
  6. customthe obtained residue was purified by column chromatography on silica gel (eluent: ethyl acetate/hexane=1/5)

Quellen und Nachweise

ORD-Eintrag
ord-1715fa63a7584bdcb58838eb27113854
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07888487B2

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