seem OK?

[abc123]

under N2 at -78C when adding Li for about 20 mins then bring to room temp...would have to be ahydrous 

   
                     NH2-CH3
C6H5-CH(OH)-CH2-CH3

+ (CH3)-C-Li ===>

                             NH(t-butyl-Li)CH3
C6H5-CH(t-butyl-Li)-CH2CH3


+ Cl-TMS  ==>


                          NH(Si(CH3)3)CH3
C6H5-CH(Si(CH3)3)CH2CH3


+ sat KF ==> ??


would tert-butyl-Li swap the OH? ..it should?

The t-butyl-Li will definately attach to the amine and swap with the silane

sat KF will rip of the silanes

any think this would work?

abc123
Dad made whisky and he made it well, cost two dollars....burned like hell......GD

[abc123]

swim is preety sure this would work if t-butyl-Li can replace an hydroxide on a benzillic carbon

would that happen?
Dad made whisky and he made it well, cost two dollars....burned like hell......GD

[Osmium]

> would that happen?

No, unfortunately not. It will produce the Li salt of the benzyl alcohol. The benzylic OH can't be replaced that way.