Question

D is an intermediate in the synthesis of rosiglitazone (trade name Avandia), a drug used for type 2 diabetes. Suggest two different methods to prepare the ether in D by substitution reactions.

Short answer

The intermediate D can be synthesized using the given methods:

i. Williamson’s ether synthesis

Step-by-step solution

Intermediate

The transient species formed during the conversion of reactants to products is termed intermediate.

The intermediate is short-lived and has more energy than the reactants and products.

Williamson’s ether synthesis

The reaction of an alcohol with an alkyl halide in the presence of a base yields an ether $\left(R-O-R^{\text{'}}\right)R,R^{\text{'}}=alkyl/arylgroups$. This reaction is named Williamson’s ether synthesis.

Synthesis of the intermediate D

The methods that can be used to synthesize D are given below.