The synthesis of suprofen, a potent non-steroidal anti-inflammatory drug, from thiophene is proposed following the sequence of reactions shown below. H3C. `N' CHз (DMF) РОСЗ steps `s Na,CO3, H20 CI H thiophene Q AICI3 CH3 2-(1-phenylethyl)- 1,3-dioxolane P.

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
Chapter22: Reactions Of Benzene And Its Derivatives
Section: Chapter Questions
Problem 22.28P
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Provide the mechanism for the Friedel-Crafts acylation reaction of compound Q and 2-(1- phenylethyl)-1,3-dioxolane that leads to the formation of intermediate R. 

 

The synthesis of suprofen, a potent non-steroidal anti-inflammatory drug, from thiophene is proposed
following the sequence of reactions shown below.
H3C
H.
CHз (DMF)
POCI3
steps
Na,CO3, H20
H
CI
thiophene
AICI3
CH3
2-(1-phenylethyl)-
1,3-dioxolane
steps
HO2C
S.
CH3
CH3
R
suprofen
Transcribed Image Text:The synthesis of suprofen, a potent non-steroidal anti-inflammatory drug, from thiophene is proposed following the sequence of reactions shown below. H3C H. CHз (DMF) POCI3 steps Na,CO3, H20 H CI thiophene AICI3 CH3 2-(1-phenylethyl)- 1,3-dioxolane steps HO2C S. CH3 CH3 R suprofen
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