Réaction #464129

Équation de réaction

Phosphonoate

Diethyl 1-methoxy-1-(3-chloro-5-methoxyphenyl)methane phosphonate

2-adamantanone

lithium diisopropylamide

→

enol ether

Rendement 56.0%

3-Chloro-5-methoxy-1-(methoxytricyclo[3,3,1,13,7 ]dec-2-ylidenemethyl)benzene

Rendement 56.0%

Solvants

THF

THF

Conditions de réaction

Traitement

1. 1
   TempératureThe reaction was slowly warmed to room temperature over 2 h
2. 2
   AutreThe solution was partitioned between EtOAc/NH4Cl
3. 3
   Séchagedried over Na2SO4
4. 4
   Autreevaporated
5. 5
   Autrepurified by silica gel chromatography (2% EtOAc/hexanes)

Mode opératoire

Phosphonoate 8 (4.62 g, 14 mmol) and 2-adamantanone (2.58 g, 17 mmol) were dissolved in anhydrous THF (35 ml) under argon and cooled to -68° C. Dropwise addition of lithium diisopropylamide (18.6 mmol) in anhydrous THF (20 ml) at -68° C. generated the ylid, followed by subsequent olefination of the ketone. The reaction was slowly warmed to room temperature over 2 h and then stirred at 75° C. for 1 h. The solution was partitioned between EtOAc/NH4Cl, dried over Na2SO4, evaporated and purified by silica gel chromatography (2% EtOAc/hexanes), yielding 2.5 g (55%) of enol ether 9 as an oil.

Source