Hydrochloric Acid → [1-phenyl-5-(phenylamino)-1H-pyrazol-3-yl]methanol

HRID 2194708Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2194708
[C:1]1([N:7]2[C:11]([NH:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[CH:10][C:9]([C:19](OCC)=[O:20])=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].C([Al+]CC(C)C)C(C)C.Cl>O1CCCC1.C1(C)C=CC=CC=1>[C:1]1([N:7]2[C:11]([NH:12][C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)=[CH:10][C:9]([CH2:19][OH:20])=[N:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 21225700DiisobutylaluminumhydrideHCID 68410675ethyl 1-phenyl-5-(phenylamino)-1H-pyrazole-3-carboxylate

Produkt 1

HCID 68411083[1-phenyl-5-(phenylamino)-1H-pyrazol-3-yl]methanolAusbeute 106,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A solution of ethyl 1-phenyl-5-(phenylamino)-1H-pyrazole-3-carboxylate (345 mg) in tetrahydrofuran (10 mL) was cooled to −78° C., and a 1.5 mol/L solution (3.7 mL) of diisobutylaluminum hydride in toluene was added dropwise. After stirring at 0° C. for 1 hr, the mixture was treated with 1 mol/L hydrochloric acid, and extracted with ethyl acetate. The extract was washed with 1 mol/L hydrochloric acid, water, saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent:hexane-ethyl acetate=2:1→1:2) to give the title compound as a pale-yellow oil (yield 318 mg, yield quantitative).

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with 1 mol/L hydrochloric acid, water, saturated aqueous sodium hydrogen carbonate solution and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluent:hexane-ethyl acetate=2:1→1:2)

Quellen und Nachweise

ORD-Eintrag
ord-178ebe5f66614d05a861e3a8d840ce8d
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08334301B2

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