Reaktion #213916

Reaktionsgleichung

hydrochloric acid

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

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

dioxane

→

title compound

2-(8-hydroxy-7-oxo-octyl)cyclopent-2-en-1-one

Lösungsmittel

brine

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONA mixture of 6.3 g
2. 2
   workup.ADDITIONTo this mixture is added 25 ml
3. 3
   Extraktionextracted with ether
4. 4
   WaschenThe ether solution is washed with saturated sodium bicarbonate
5. 5
   Trocknendried over magnesium sulfate
6. 6
   SonstigeThe solvent is removed
7. 7
   Sonstigethe residue is chromatographed on a dry column of silica gel eluting with ether containing 2% acetic acid
8. 8
   Sonstigeto give 1.7 g

Vorschrift

A mixture of 6.3 g. of 2-[6-(chloroformyl)hexyl]-cyclopent-2-en-1-one (Example 75) and 16 g. of tris-trimethylsilyloxyethylene (Example 74) are stirred at 90° to 100° C. under argon for one hour. To this mixture is added 25 ml. of dioxane and 10 ml. of 0.6N hydrochloric acid. The mixture is heated at 80° C. for 30 minutes. The mixture is poured into brine and extracted with ether. The ether solution is washed with saturated sodium bicarbonate and dried over magnesium sulfate. The solvent is removed and the residue is chromatographed on a dry column of silica gel eluting with ether containing 2% acetic acid to give 1.7 g. of the title compound (Rf =0.45).

Quelle