Dimethyl-pyrrolidin-3-one

Synthesised from 3-methyl-butan-2-one (7).⁶

Generation of silyl enol ether from (9)

A variety of experimental conditions have been investigated for the generation of silyl enol ethers from pyrrolidinone (9).

      
Experimental Conditions                             Result
                       
KH, TMSCl, -78 °C, THF			starting material                                  
                                                                                    
KH, TESCl, -78 °C, THF			silyl enol ether and starting pyrrolidinone        
                                                                                     
LDA, TESCl, -78 °C, THF			starting material                                  
                                                                                     
KH, TBDMSCl, 0 °C, THF			silyl enol ether                                   
                                                                                     

The TBDMS silyl enol ether is stable relative to the TES silyl enol ether.

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Summary