Réaction #548455

Équation de réaction

ether

1-chloro-3-triphenylmethoxyhexane

1-chloro-3-triphenylmethoxy hexane

dimethylsulfoxide

water

hydrochloric acid

DMSO

→

5-triphenylmethoxy-1-octyne

Conditions de réaction

Traitement

1. 1
   Températurewhile cooling in an ice bath
2. 2
   AutreThe phases are separated
3. 3
   Extractionthe aqueous phase is extracted with ether-petroleum ether
4. 4
   LavageThe combined extracts are washed successively with water and saturated sodium chloride solution
5. 5
   Séchagedried over magnesium sulfate
6. 6
   Concentrationconcentrated
7. 7
   AutreThe product is then purified by column chromatography of the residue on Florisil

Mode opératoire

To a stirred solution of 32.2 g. (85 mmoles) of 1-chloro-3-triphenylmethoxyhexane (Example 750a) in 25 ml. of dimethylsulfoxide (DMSO) is added a solution of 9.4 g. (102 mmoles) of lithium acetylide-ethylene diamine complex in 60 ml. of DMSO during 10 minutes while maintaining a temperature of 25°-30° C. After 3.5 hours the mixture is diluted with ether and treated successively with water and 4N hydrochloric acid while cooling in an ice bath. The phases are separated, and the aqueous phase is extracted with ether-petroleum ether. The combined extracts are washed successively with water and saturated sodium chloride solution dried over magnesium sulfate, and concentrated. The product is then purified by column chromatography of the residue on Florisil.

Source