Proposed Synthesis of Compound D
Pam Crall
Discussion
Put ethyl bromide in NaNH2 with ethyne to form butyne. Add H2 with Lindlar’s catalyst to form 1-butene. To half the 1-butene, add HBr. This forms the Markovnikov product 2-bromo-butane (p. 145 in Bruice). To this, add magnesium in diethyl ether to form a Grignard reagent. To the other half of 1-butene, add HBr in peroxide to form the anti-Markovnikiv product 1-butanol (p. 163 in Bruice). To this primary alcohol add PCC to form an aldehyde (p. 798 in Bruice). Add the Grignard reagent made with the first half of the 1-butene to form the product (p. 742 in Bruice).