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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.

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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

What reagents are needed to convert 2-methylpropene [CH3C=CH2]to each compound? More than one step may be required.

a.

b.

c.

One step in the synthesis of the nonsteroidal anti-inflammatory drug rofecoxib (trade name Vioxx) involves Suzuki coupling of A and B. What product is formed in this reaction?

What ring-closing metathesis product is formed when each substrate is treated with Grubbs catalyst under high-dilution conditions?

a.

b.

c.

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

Metathesis reactions can be carried out with two different alkene substrates in one reaction mixture. Depending on the substitution pattern around the C=C, the reaction may lead to one major product or a mixture of many products. For each pair of alkene substrates, draw all metathesis products formed. (Disregard any starting materials that may also be present at equilibrium.) With reference to the three examples, discuss when alkene metathesis with two different alkenes is a synthetically useful reaction.
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