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Chapter 26: Q26P (page 1049)

Identify X, an intermediate that was converted to eletriptan (trade name Relpax), a drug used to treat migraines.

Short Answer

Expert verified

The reaction between an alkene and an alkyl halide group in the presence of a base and a catalyst (palladium) is known as the Heck reaction. In this reaction, an alkene is formed.

Step by step solution

01

Heck reaction

The reaction between an alkene and an alkyl halide group in the presence of a base and a catalyst (palladium) is known as the Heck reaction. In this reaction, an alkene is formed.

02

Mechanism of Heck reaction  

  • In the first step, the divalent palladium catalyst reacts with the alkyl halide (RX) to form an organo-palladium compound.
  • In the second step, the (R) group and palladium (Pd) from the organopalladium compound add to the C=C such that Pd bonds with the more substituted carbon.
  • In the third step, the elimination of hydrogen and palladium takes place. Then, by reductive elimination, the initial palladium catalyst is regenerated.
03

Products of the given reaction

Compound X is shown here under.

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Most popular questions from this chapter

Draw the products formed in each reaction.

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f.

g.

h.

Draw the coupling product formed when each pair of compounds is treated with Pd(OAc)2, P(o-tolyl)3, and Et3N.

Draw the product formed from the ring-closing metathesis of each compound. Then, devisea synthesis of each metathesis starting material using any of the following compounds: CH2(CO2Et)2, alcohols with less than five carbons, and any needed organic and inorganicreagents.

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Synthesize each product from the given starting materials using an organocuprate coupling reaction.

Draw the product formed from the ring-closing metathesis of each compound. Then, devise a synthesis of each metathesis starting material from benzene, alcohols with less than five carbons, and any needed organic and inorganic reagents.

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