تفاعل #444813

معادلة التفاعل

Phosphonate

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

2-adamantanone

lithium diisopropylamide

→

enol ether

المردود 56.0%

3-Chloro-5-methoxy-1-(methoxytricyclo[3.3.1.13.7 ]dec-2-ylidenemethyl)benzene

المردود 56.0%

المذيبات

THF

THF

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThe reaction was slowly warmed to room temperature over 2 h
2. 2
   أخرىThe solution was partitioned between EtOAc/NH4Cl
3. 3
   أخرىdried over Na2 SO4
4. 4
   أخرىevaporated
5. 5
   أخرىpurified by silica gel chromatography (2% EtOAc/hexanes)

الإجراء التجريبي

Phosphonate 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 Na2 SO4, evaporated and purified by silica gel chromatography (2% EtOAc/hexanes), yielding 2.5 g (55%) of enol ether 9 as an oil.

المصدر