반응 #8570

반응 방정식

water

potassium hydroxide

(2S)-2-(2,3,4-trifluoroanilino)propanol

diethylethoxymethylenemalonate

→

title compound

수율 90.2%

Diethyl [2,3,4-trifluoro[(1S)-2-hydroxy-1-methylethyl]anilino]methylenemalonate

수율 90.2%

용매

DMF

DMF

반응 조건

후처리

1. 1
   기타the liquid reaction mixture
2. 2
   추출was extracted with a solvent mixture of ethyl acetate and n-hexane (3:2)
3. 3
   세척The organic layer was washed with water
4. 4
   건조dried over anhydrous magnesium sulfate
5. 5
   기타After evaporating the solvent, IPE
6. 6
   workup.ADDITIONwas added to the obtained residue
7. 7
   기타The crystals thus precipitated
8. 8
   여과were collected by filtration
9. 9
   기타the moist product thus obtained
10. 10
    기타was dried under reduced pressure

실험 절차

At room temperature, potassium hydroxide (330 mg) and tetrabutylammonium hydrogensulfate (82.7 mg) were dissolved in DMF (15 ml). After adding a solution (5 ml) of (2S)-2-(2,3,4-trifluoroanilino)propanol (1 g, 99.8% ee) and diethylethoxymethylenemalonate (2.09 g) in DMF, the resultant mixture was stirred for 1 hour. After adding water, the liquid reaction mixture was extracted with a solvent mixture of ethyl acetate and n-hexane (3:2). The organic layer was washed with water and dried over anhydrous magnesium sulfate. After evaporating the solvent, IPE was added to the obtained residue and the mixture was stirred at 0° C. for 1 hour. The crystals thus precipitated were collected by filtration and the moist product thus obtained was dried under reduced pressure. Thus, the title compound (1.65 g, 99. 8% ee) was obtained as colorless crystals. The 1H-NMR and IR spectral data of this product was identical with those of the compound obtained in Example 63.

출처