반응 #50123

반응 방정식

water

4-Acetoxy-2-methyl-1-chloro-2-butene

sodium formate

→

4-acetoxy-2-methyl-2-buten-1-ol formate

수율 95.0%

용매

dimethylformamide

반응 조건

후처리

1. 1
   온도under heating
2. 2
   기타After completion of the reaction
3. 3
   workup.ADDITIONthe reaction mixture was poured into ice-
4. 4
   추출extracted with ether (50 ml) three times
5. 5
   건조The extracted ether layer was dried over anhydrous sodium sulfate
6. 6
   기타Evaporation of the ether
7. 7
   기타followed by purification by silica gel column chromatography (ethyl acetate-hexane (=1:3))

실험 절차

4-Acetoxy-2-methyl-1-chloro-2-butene (8.13 g, 50 mmol) was dissolved in dimethylformamide (25 ml) and placed in a 100 ml four neck flask. To this were added sodium formate powder (6.80 g, 100 mmol, 2 equivalents) and tetra n-butylammonium bromide (0.81 g, 2.5mmol, 5 mol %). The mixture was stirred at 40° C. for 24 hours under heating. After completion of the reaction, the reaction mixture was poured into ice-cooled water (about 30 ml)and extracted with ether (50 ml) three times. The extracted ether layer was dried over anhydrous sodium sulfate. Evaporation of the ether followed by purification by silica gel column chromatography (ethyl acetate-hexane (=1:3)) gave 4-acetoxy-2-methyl-2-buten-1-ol formate (8.18 g, 47.5 mmol; Yield: 95.0%).

출처