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Chapter 26: Q 26. (page 1070)

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

Short Answer

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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 hereunder.

Compound X

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Most popular questions from this chapter

Identify reagents A and B in the following reaction scheme. This synthetic sequence was used to prepare the C18 juvenile hormone (Figure 20.6).

Sulfur ylides, like the phosphorus ylides of Chapter 21, are useful intermediates in organic synthesis. Methyl trans-chrysanthemate, an intermediate in the synthesis of the insecticide pyrethrin I (Section 26.4), can be prepared from diene A and a sulfur ylide. Draw a stepwise mechanism for this reaction.

What product is formed when each alkene is treated with and Zn(Cu)?

a.

b.

c.

What stereoisomers are formed when trans-hex-3-ene is treated withCH2I2 and Zn(Cu)?

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