Objective

Isolating the "demethylated" product of the reaction of furan containing Ugi products with TFA, as explained here.

Steps

  1. Dissolve 50 mg of Ugi product (for example 62E) 500 ul CDCl3 and take H NMR
  2. Add 500 ul TFA, mix and take NMR after 5 mins
  3. Monitor by NMR after approximately 10, 20, 40, 80, etc. min until the reaction is complete (should be around 48 hours)
  4. Pour into 10 ml of 10% NaOH and 10 ml of methylene chloride. Verify that the water layer is basic using pH paper.
  5. Wash twice with 10 ml of methylene chloride then combine all the organic phases.
  6. Add MgSO4 until fluffy when stirred, filter and evaporate.
  7. Get the weight and take NMR.