Reaktion #213915

Reaktionsgleichung

sodium hydride

2-(6-carboxyhexyl)-cyclopent-2-en-1-one

oxalyl chloride

→

title compound

2-[6-(chloroformyl)hexyl]cyclopent-2-en-1-one

Lösungsmittel

tetrahydrofuran

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONTo a suspension of 1.94 g
2. 2
   workup.ADDITIONAfter the addition
3. 3
   workup.STIRRINGthe mixture is stirred for 1 hour 15 minutes
4. 4
   workup.STIRRINGThe mixture is stirred at 0° C. for 30 minutes and at room temperature for 30 minutes
5. 5
   workup.ADDITIONThe solution is diluted with 500 ml
6. 6
   Filtrationof ether and filtered through Celite
7. 7
   SonstigeThe solvent is removed from the filtrate
8. 8
   Extraktionthe residue is extracted with hot hexane twice
9. 9
   SonstigeThe hexane is removed
10. 10
    Sonstigeto give 16.0 g

Vorschrift

To a suspension of 1.94 g. (0.08 mol) of sodium hydride in 100 ml. of tetrahydrofuran is added with stirring under argon dropwise a solution of 17 g. (0.08 mol) of 2-(6-carboxyhexyl)-cyclopent-2-en-1-one in 160 ml. of tetrahydrofuran. After the addition is complete, the mixture is stirred for 1 hour 15 minutes. The mixture is cooled to 0° C. and 13 ml. of oxalyl chloride is added. The mixture is stirred at 0° C. for 30 minutes and at room temperature for 30 minutes. The solution is diluted with 500 ml. of ether and filtered through Celite. The solvent is removed from the filtrate and the residue is extracted with hot hexane twice. The hexane is removed to give 16.0 g. of the title compound.

Quelle