Proposed Synthesis of Compound E

Pam Crall

 

 

Discussion

 

Begin by adding ethyl iodide to ethyne in sodium amide (p. 257). This forms 2-pentyne. To this, add HBr in one equivalent to form 2-bromo-2-pentene and 3-bromo-2-pentene (p. 246). The second is discarded. The first is made into a Grignard reagent using magnesium in diethyl ether. After an epoxide is made using MCPBA, the Grignard reagent is added to form the product.