Reacción #213885

Ecuación de reacción

magnesium

5-chloro-2-pentanone

dibromoethane

propargyl bromide

propargyl bromide

ammonium chloride

→

product

7-Chloro-4-hydroxy-4-methyl-1-heptyne

Disolventes

ether

ether

ether

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONTo a mixture of 6.69 g
2. 2
   Temperaturato maintain vigorous reflux
3. 3
   workup.STIRRINGThe mixture is stirred an additional 15 minutes
4. 4
   OtroThe ether layer is decanted
5. 5
   Filtraciónfiltered
6. 6
   LavadoThe solids are washed with ether which
7. 7
   Filtraciónis also filtered
8. 8
   LavadoThe combined ether filtrates are washed with water
9. 9
   Secadodried over magnesium sulfate
10. 10
    Otrothe solvent removed

Procedimiento

To a mixture of 6.69 g. of magnesium in 20 ml. of ether under argon, is added 0.1 g. of mercuric chloride and 0.1 g. of dibromoethane. The mixture is stirred for 10 minutes and 0.5 ml. of propargyl bromide is added. A 50 ml. portion of ether is added, followed by a solution of 30 g. of 5-chloro-2-pentanone and 32.55 g. of propargyl bromide in 45 ml. of ether with stirring, at a rate to maintain vigorous reflux. The mixture is stirred an additional 15 minutes, cooled to -5° C. and an ice cold saturated solution of ammonium chloride is added dropwise. The ether layer is decanted and filtered. The solids are washed with ether which is also filtered. The combined ether filtrates are washed with water, dried over magnesium sulfate and the solvent removed giving the product as an orange oil.

Fuente