Réaction #457491

Équation de réaction

nBuLi

2-adamantanone

2-adamantanone

phosphonate

nBuLi

Phosphonate

Diethyl 1-methoxy-1-(3-methoxy-5-trifluoroacetamidophenyl)methane Phosphonate

→

enol ether

3-Methoxy-5-trifluoroacetamido-1-(methoxytricyclo[3.3.1.13,7 ]-dec-2-ylidene-methyl)benzene

Solvants

THF

THF

THF

Conditions de réaction

Traitement

1. 1
   Températurecooled to -68° C. under argon in a separate flask
2. 2
   workup.ADDITIONis slowly added to the ylid over an hour
3. 3
   workup.STIRRINGthe reaction mixture is stirred for 2 h
4. 4
   Températurewhile warming to room temperature
5. 5
   TempératureThe reaction is then heated
6. 6
   Températureat reflux for 1 h
7. 7
   Températurecooled
8. 8
   Autrequenched
9. 9
   Autreby partitioning with EtOAc and saturated NH4Cl
10. 10
    SéchageThe organic layer is dried over Na2SO4
11. 11
    Autrechromatographed with EtOAc/hexanes on a silica gel column

Mode opératoire

Phosphonate 30, dissolved in anhydrous THF, is cooled to -68° C. under an argon atmosphere. Similarly, 2-adamantanone (1.1 eq) is dissolved in anhydrous THF and cooled to -68° C. under argon in a separate flask. To the phosphonate solution is added 2.5M nBuLi at -68° C. under argon until the red color of the ylid persists. At this point, 1.2 eq nBuLi is added to complete the ylid formation and the resulting colored solution is stirred at -68° C. for 5 min. While maintaining the low temperature, 2-adamantanone in THF is slowly added to the ylid over an hour. After the final addition of ketone, the reaction mixture is stirred for 2 h while warming to room temperature. The reaction is then heated at reflux for 1 h, cooled and quenched by partitioning with EtOAc and saturated NH4Cl. The organic layer is dried over Na2SO4 and chromatographed with EtOAc/hexanes on a silica gel column to give enol ether 31.

Source