Reaktion #50123

Reaktionsgleichung

water

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

sodium formate

→

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

Ausbeute 95.0%

Lösungsmittel

dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturunder heating
2. 2
   SonstigeAfter completion of the reaction
3. 3
   workup.ADDITIONthe reaction mixture was poured into ice-
4. 4
   Extraktionextracted with ether (50 ml) three times
5. 5
   TrocknenThe extracted ether layer was dried over anhydrous sodium sulfate
6. 6
   SonstigeEvaporation of the ether
7. 7
   Sonstigefollowed by purification by silica gel column chromatography (ethyl acetate-hexane (=1:3))

Vorschrift

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%).

Quelle