Chapter 19, Problem 19.50P

Interpretation Introduction

Interpretation:

Problems associated with the given synthesis are to be explained. A way to carry out the given transformation is to be suggested.

Concept introduction:

Lithium diisopropylamide (LDA) is strong base and selectively the kinetic enolate, which leads to alkylation at the less substituted $\text{α}$ C atom and also can abstract the alcoholic proton to form the ${\text{O}}^{\text{-}}$ anion.

To protect an alcoholic group, it is converted to its silyl ether derivatives like TBDMSCl, which is stable under the basic condition.