Identify the major product of the following reaction sequence: [ (ii) NaOH, ] (i) 4 eq. NaOMe, Product

Step-by-step solution

The given reaction is the Weiss-Cook reaction. The first reactant is dimethyl 3-oxopentanedioate (dimethyl acetonedicarboxylate). The presence of the coefficient 2 indicates that 2 equivalents of this diester react with 1 equivalent of glyoxal. In the first step, 4 equivalents of NaOMe are used to deprotonate the 4 active methylene groups (two from each equivalent of the diester). The enolates undergo a double condensation with the two aldehyde groups of glyoxal, followed by cyclization. This forms the bicyclic int