Q28. - Organic Chemistry

Question

Question: Nabumetone is a pain reliever and anti-inflammatory agent sold under the brand name of Relafen.

a. Write out a synthesis of nabumetone from ethyl acetoacetate.

b. What ketone and alkyl halide are needed to synthesize nabumetone by direct enolate alkylation?

Step-by-Step Solution

Answer

Answer

 

a. A synthesis of nabumetone from ethyl acetoacetate is shown in the following method:

b. A synthesis of nabumetone from direct enolation using ketone and halide is shown in the following method:

Step 1: Choosing the acetoacetic ester starting materials

The retrosynthetic pathway is required to obtain the correct ethyl acetoacetate and halide.

Representation of the retrosynthetic analysis

Step 2: Choosing the carbonyl compound and halides

To select the correct ketone and alkyl halide used, the retrosynthetic pathway is required for obtaining them.

Representation of the retrosynthetic analysis

Step 3: Forward steps for the synthesis of the product

The forward steps required for the synthesis of the product are shown below:

Representation of the forward pathway