반응 #477787

반응 방정식

sodium hydride

triethyl 2-fluoro-2-phosphonoacetate

ammonium chloride

3′-methylaminobiphenyl-4-carbaldehyde

→

ethyl 2-fluoro-3-(3′-methylaminobiphenyl-4-yl)acrylate

수율 82.3%

용매

tetrahydrofuran

tetrahydrofuran

반응 조건

후처리

1. 1
   workup.ADDITIONis then added dropwise
2. 2
   workup.STIRRINGThe reaction mixture is stirred at room temperature overnight
3. 3
   추출extracted with ethyl acetate
4. 4
   세척washed with water
5. 5
   건조dried over sodium sulfate
6. 6
   기타The solvent is evaporated off
7. 7
   기타the residue (2.2 g) is purified by chromatography on a column of silica
8. 8
   세척eluted with an 85/15 heptane/ethyl acetate mixture

실험 절차

382 mg (9.5 mmol) of sodium hydride are added to a solution of 1.9 mL (9.5 mmol) of commercial triethyl 2-fluoro-2-phosphonoacetate in 10 mL of tetrahydrofuran. The reaction mixture is stirred at room temperature for 40 minutes. A solution of 803 mg of 3′-methylaminobiphenyl-4-carbaldehyde prepared as described in Example 5b (3.8 mmol) in 8 mL of tetrahydrofuran is then added dropwise. The reaction mixture is stirred at room temperature overnight. The reaction medium is poured into saturated ammonium chloride solution and extracted with ethyl acetate. The organic phases are combined, washed with water and dried over sodium sulfate. The solvent is evaporated off and the residue (2.2 g) is purified by chromatography on a column of silica eluted with an 85/15 heptane/ethyl acetate mixture. 936 mg (82%) of ethyl 2-fluoro-3-(3′-methylaminobiphenyl-4-yl)acrylate are obtained in the form of a yellow oil.

출처