Hydrolysis Grignard acyl addition products

Attempts to directly form enamide 44 from methyl Grignard addition and trapping with acetic anhydride resulted in a variety of products including C-acylation as well as the imine (or the ketone 31, the result of hydrolysis of this intermediate). An investigation into this reaction revealed that both the addition and the acylation were sensitive to both solvent and temperature. The effect of additives was investigated, and it was discovered that the use of MeLi with lithium bromide had a dramatic effect on the reaction profile (Scheme 5.21). 

---