Réaction #64189

Équation de réaction

water

lithium diisopropylamide

2-adamantanone

4-[1-(imidazolyl)methyl]benzonitrile

→

4-[2-hydroxy-adamant-1-yl-1-(imidazolyl)methyl]benzonitrile

Solvants

tetrahydrofuran

tetrahydrofuran

Conditions de réaction

Traitement

1. 1
   workup.STIRRINGfurther stirred for 1 hour
2. 2
   Températureheated to 25°
3. 3
   Extractionthe mixture is extracted three times with ethyl acetate
4. 4
   Lavagewashed neutral with water
5. 5
   Séchagedried over sodium sulfate
6. 6
   Concentrationconcentrated to dryness under vacuum

Mode opératoire

5.0 g of 4-[1-(imidazolyl)methyl]benzonitrile is dissolved in 100 ml of tetrahydrofuran and combined at -50° with 20 ml of 1.5-molar solution of lithium diisopropylamide in tetrahydrofuran, stirred for 0.5 hour at -60° combined With 4 3 g of 2-adamantanone, further stirred for 1 hour, and heated to 25°. Then water is added, the mixture is extracted three times with ethyl acetate, washed neutral with water, dried over sodium sulfate, and concentrated to dryness under vacuum, thus obtaining 6.66 g of crude 4-[2-hydroxy-adamant-1-yl-1-(imidazolyl)methyl]benzonitrile.

Source