Ethanol → 1-methyl-5-(2-phenylethenyl)-1H-pyrazole

HRID 238358

Reaktionsgleichung

[CH3:1][N:2]1[C:6](B2OC(C)(C)C(C)(C)O2)=[CH:5][CH:4]=[N:3]1.Br[CH:17]=[CH:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(=O)([O-])[O-].[K+].[K+].C(O)C>C(OCC)(=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CN(C)C=O>[CH3:1][N:2]1[C:6]([CH:17]=[CH:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:5][CH:4]=[N:3]1

Komponenten

Reaktionsbedingungen

Temperatur: 75 °C

Versuchsvorschrift

Under a nitrogen atmosphere, a mixture of 1-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (1.50 g), β-bromostyrene (1.45 g), bis(triphenylphosphine)palladium(II) dichloride (506 mg), potassium carbonate (1.30 g), ethanol (3.8 mL) and dimethylformamide (7.5 mL) was stirred at 75° C. for 6 hours. Thereafter, 13-bromostyrene (1.45 g) was further added to the reaction solution, and the obtained solution was then stirred at 75° C. for 4 hours. Subsequently, the reaction solution was diluted with ethyl acetate, and was then washed with water. The organic layer was dried over anhydrous magnesium sulfate, and was then concentrated under a reduced pressure. The residue was purified by column chromatography (silica gel 60N, hexane:ethyl acetate=4:1 to 3:1), so as to obtain the title compound (990 mg) in the form of a light yellow solid.

Aufarbeitung

stirringthe obtained solution was then stirred at 75° C. for 4 hours
washwas then washed with water
dry with materialThe organic layer was dried over anhydrous magnesium sulfate
concentrationwas then concentrated under a reduced pressure
customThe residue was purified by column chromatography (silica gel 60N, hexane:ethyl acetate=4:1 to 3:1)

Quellen und Nachweise

ORD-Eintrag: ord-cdf1f42d84c94674be51e5c49efc0fb6
Quelldatensatz: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08642626B2

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