反応 #665965

反応方程式

hydrochloric acid

4-chloro-3-nitrobenzaldehyde

benzyltriphenylphosphonium bromide

sodium hydride

→

2-chloro-5-((Z)-2-phenylvinyl)-1-nitrobenzene

収率 56.5%

溶媒

toluene

反応条件

後処理

1. 1
   抽出the resulting mixture was extracted with methylene chloride
2. 2
   洗浄The extract was washed with brine
3. 3
   乾燥dried over anhydrous magnesium sulfate
4. 4
   その他the solvent was removed under reduced pressure
5. 5
   その他The residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=10/1)

実験手順

To a suspension of 4-chloro-3-nitrobenzaldehyde (1 g) and benzyltriphenylphosphonium bromide (2.34 g) in toluene (35 mL) was added sodium hydride (55%, 0.28 g), and the mixture was stirred at room temperature overnight. To the reaction mixture was added 1 mol/L hydrochloric acid, and the resulting mixture was extracted with methylene chloride. The extract was washed with brine and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=10/1) to give 2-chloro-5-((Z)-2-phenylvinyl)-1-nitrobenzene (0.79 g). The obtained 2-chloro-5-((Z)-2-phenyl -vinyl)-1-nitrobenzene (0.16 g) was dissolved in ethanol (6 mL) -methanol (2 mL). To the solution was added 5% rhodium-carbon powder (20 mg) and morpholine (5 mg), and the mixture was stirred at room temperature under a hydrogen atmosphere overnight. The insoluble material was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=5/1) to give the title compound (87 mg).

出典