反応 #595105

反応方程式

water

benzyltriphenylphosphonium bromide

potassium carbonate

3-[4-(Trifluoromethyl)phenyl]-1H-pyrazole-5-carbaldehyde

→

title compound

収率 56.0%

5-(2-phenylethyl)-3-[4-(trifluoromethyl)phenyl]-1H-pyrazole

収率 56.0%

溶媒

tetrahydrofuran

N,N-dimethylformamide

ethanol

反応条件

後処理

1. 1
   抽出the mixture was extracted with ethyl acetate
2. 2
   乾燥The ethyl acetate layer was dried over anhydrous magnesium sulfate
3. 3
   濃縮concentrated
4. 4
   その他The residue was purified by silica gel column chromatography (10%-65% ethyl acetate/hexane)
5. 5
   その他to give colorless crystals
6. 6
   workup.STIRRINGUnder an atmospheric hydrogen atmosphere, the mixture was stirred at room temperature for 2 hr
7. 7
   ろ過The catalyst was filtered off
8. 8
   濃縮the filtrate was concentrated

実験手順

3-[4-(Trifluoromethyl)phenyl]-1H-pyrazole-5-carbaldehyde (1.20 g, 5.0 mmol) was dissolved in N,N-dimethylformamide (10 mL), and benzyltriphenylphosphonium bromide (3.25 g, 7.5 mmol) and potassium carbonate (2.76 g, 20.0 mmol) were added. The mixture was stirred at room temperature for 14 hr. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was dried over anhydrous magnesium sulfate and concentrated. The residue was purified by silica gel column chromatography (10%-65% ethyl acetate/hexane) to give colorless crystals. The colorless crystals were dissolved in tetrahydrofuran (30 mL) and ethanol (30 mL), and 10% palladium-carbon (50% water-containing product, 500 mg) was added. Under an atmospheric hydrogen atmosphere, the mixture was stirred at room temperature for 2 hr. The catalyst was filtered off, and the filtrate was concentrated to give the title compound (880 mg, yield 56%, 2 steps) as colorless crystals.

出典