Réaction #75329

Équation de réaction

cyclopentanone

water

→

residue

Rendement 197.3%

1-[Prop-1-en-1-yl)spiro[2.4]heptan -4-one

Rendement 197.3%

Solvants

THF

Conditions de réaction

Traitement

1. 1
   workup.WAITAfter having been left for two supplemental hours
2. 2
   Températureat reflux
3. 3
   workup.STIRRINGstirring
4. 4
   workup.ADDITIONpoured onto ice
5. 5
   Extractionextracted with ether
6. 6
   LavageThe combined organic extracts were successively washed with 1N HCl
7. 7
   AutreBy the evaporation of the volatile components

Mode opératoire

2.1 g (25 mM) of cyclopentanone, containing 0.3% of water, in 20 ml of THF were added dropwise to the reaction mixture while stirring. After having been left for two supplemental hours at reflux and stirring, the reaction mixture was cooled to room temperature, poured onto ice and extracted with ether. The combined organic extracts were successively washed with 1N HCl, a diluted aqueous solution of sodium bicarbonate and finally water. By the evaporation of the volatile components there were obtained 3.7 g of residue which, upon bulb-distillation gave 2.25 g (yield 67%) of the desired spiro-heptanone having a b.p. of 110°-125°/10 Torr. The assessed purity is of about 90%. The product represents an isomeric mixture containing cis- and trans- 1-(prop-1-en-1-yl) spiro [2.4]heptan-4-one in a 2:1 respective weight ratio.

Source