Benzaldehyde → phenyl(3-phenyl-1H-indazol-6-yl)methanol

HRID 563392Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 563392
Br[C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[N:7][NH:8]2)=[CH:4][CH:3]=1.C([Li])CCC.[CH:22](=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C1COCC1>[C:23]1([CH:22]([C:2]2[CH:10]=[C:9]3[C:5]([C:6]([C:11]4[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=4)=[N:7][NH:8]3)=[CH:4][CH:3]=2)[OH:29])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Komponenten

5

Edukt 3

HCID 240BenzaldehydeHCID 573551936-Bromo-3-phenyl-1H-indazoleHCID 178418339Butyllithium

Produkt 1

HCID 59252831phenyl(3-phenyl-1H-indazol-6-yl)methanolAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirred solution of 6-bromo-3-phenyl-1H-indazole (109 mg, 0.40 mmol) in anhydrous THF (3 mL) was added n-butyl lithium solution (2M in hexanes, 0.47 mL, 0.94 mmol) dropwise at −78° C. under argon. The reaction mixture was stirred at −78° C. for 30 min and at −40° C. for 6 min before benzaldehyde (0.1 mL, 1 mmol) was added at −40° C. The reaction mixture was then stirred at rt for 1 hr. quenched with saturated aqueous ammonium chloride solution (5 mL) and extracted with ethyl acetate (10 mL). The ethyl acetate extract was dried (Na2SO4) and concentrated. Silica gel flash chromatography gave phenyl(3-phenyl-1H-indazol-6-yl)methanol (71 mg, 0.24 mmol, 59% yield) as a solid.

Aufarbeitung

  1. additionwas added at −40° C
  2. customquenched with saturated aqueous ammonium chloride solution (5 mL)
  3. extractionextracted with ethyl acetate (10 mL)
  4. extractionThe ethyl acetate extract
  5. dry with materialwas dried (Na2SO4)
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-162939de5250419d992c34007f545513
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08067447B2

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