A synthesis of N-tosyl indole 15 starting from the pyrrole-2-carboxaldehyde 11 and acetal containing alkyl bromide 12 is shown overleaf. Identify intermediate 13 formed on treating the alkyl bromide 12 with magnesium. Explain how 13 then reacts with pyrrole 11 and identify compound 14 formed after aqueous work-up. Show how 14 is finally converted into indole 15 on treatment with acid (hint: the acetal group in 12 is a protected form of an aldehyde). Give mechanisms for each step of the transformation. Br H₂SO4 (aq) heat Ts 11 Ts= Mg 13 12 14 1 Ts 15
A synthesis of N-tosyl indole 15 starting from the pyrrole-2-carboxaldehyde 11 and acetal containing alkyl bromide 12 is shown overleaf. Identify intermediate 13 formed on treating the alkyl bromide 12 with magnesium. Explain how 13 then reacts with pyrrole 11 and identify compound 14 formed after aqueous work-up. Show how 14 is finally converted into indole 15 on treatment with acid (hint: the acetal group in 12 is a protected form of an aldehyde). Give mechanisms for each step of the transformation. Br H₂SO4 (aq) heat Ts 11 Ts= Mg 13 12 14 1 Ts 15
Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter19: Enolate Anions And Enamines
Section19.9: Crossed Enolate Reactions Using Lda
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![A synthesis of N-tosyl indole 15 starting from the pyrrole-2-carboxaldehyde
11 and acetal containing alkyl bromide 12 is shown overleaf. Identify
intermediate 13 formed on treating the alkyl bromide 12 with magnesium.
Explain how 13 then reacts with pyrrole 11 and identify compound 14 formed
after aqueous work-up. Show how 14 is finally converted into indole 15 on
treatment with acid (hint: the acetal group in 12 is a protected form of an
aldehyde). Give mechanisms for each step of the transformation.
Br
H₂SO4 (aq)
heat
Ts 11
Ts=
Mg
13
12
14
Ts
15](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2F4e29cc25-6e5d-46fd-9e32-4186bf3bd863%2F18b0c652-a2ed-420c-9581-71b955aec0c2%2F65fow3q_processed.jpeg&w=3840&q=75)
Transcribed Image Text:A synthesis of N-tosyl indole 15 starting from the pyrrole-2-carboxaldehyde
11 and acetal containing alkyl bromide 12 is shown overleaf. Identify
intermediate 13 formed on treating the alkyl bromide 12 with magnesium.
Explain how 13 then reacts with pyrrole 11 and identify compound 14 formed
after aqueous work-up. Show how 14 is finally converted into indole 15 on
treatment with acid (hint: the acetal group in 12 is a protected form of an
aldehyde). Give mechanisms for each step of the transformation.
Br
H₂SO4 (aq)
heat
Ts 11
Ts=
Mg
13
12
14
Ts
15
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