Chapter 19.SE, Problem 77AP

Interpretation Introduction

Interpretation:

The synthesis of 6–methyl–5–hepten–2–one from methyl– 4–oxo pentanoate is to be given.

Concept introduction:

The synthesize required can be carried out by the following steps. i) Protecting the keto group in the ketoester by treating with a diol ii) reduction of the ester to a primary alcohol iii) oxidation of the primary alcohol to aldehyde iv) Wittig reaction of the aldehyde with a phosphorus ylide. v) removal of the acetol linkage by hydrolysis.

To give:

The synthesis of 6–methyl–5–hepten–2–one from methyl– 4–oxo pentanoate.