LECTURE #3

CHM-625, 675
A D VA N C E O R G A N I C C H E M I S T R Y- I

BS 8TH , MSC 3RD

DR. NUSRAT SHAFIQ
CHEMISTRY DEPARTMENT
CONTENTS

• Protection of Alcoholic OH group

• Ethers

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 PROTECTION OF ALCOHOLIC OH GROUP
Ethers
O
O O O O
1. OH KMnO4 H+ / H2O
HO OH
Ethers are stable towards H+ HO OH
nucleophilic conditions. O HO
O
An alcohol can be 2. ROH
R
H2O/H+
ROH
R
converted into an ether H + O O O O
H
on reaction with any
alkylating agent in the O
H+
O O
3. R OH Or
presence of a base Protection R R OTHP H+/ H2O
R OH
De-Protection

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SYNTHESIS OF PHEROMONE

It’s a good example of use of protecting groups in organic synthesis by using ether as
protecting groups

HBr DPH/H + O O
HO 6 OH HO 6
Br O O
A LiC CH 7
B 6
D
C
Br
i. LiNH2
O CH3 O CH3 O ii. C2H5Br
O O H3C Cl HO H2O/H+ O O
7 Lindard, s 7 7 7
Reduction
H3C H3C H3C H3C
G F E
Pheromone

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WHAT UNWANTED REACTION WOULD BE HAPPEN DURING
ATTEMPT
O REDUCTION OF AND HOW MIGHT BE IT PREVENTED?
O Redn. O
OH
O

The reduction of -C=O is also occurred along with -COOEt group. So it is prevented by protecting -C=O group before
reaction.
O
1. Protection O
O
2. LiAlH4
OH
3. Deprotection
Mechanism O
O
O H2O/H+ O
O O LiAlH4 O O
OH OH
O OH OH
O
O

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 WHAT UNWANTED REACTION WOULD BE HAPPEN DURING
ATTEMPT REDUCTION OF AND HOW MIGHT BE IT
PREVENTED?
O
MeO MeO
1. OMe i. Protection OH
ii. LiAlH
MeO iii. Deprotection MeO
O O
Mechanism

O O The reduction of -C=O is

MeO
MeO
OMe OMe also occurred along with -
OH OH
MeO
COOMe group. So it is
MeO
O
O O prevented by protecting -
C=O group before reaction.
MeO LiAlH4
OH
MeO
H2O/H+ OH
MeO
O MeO
O O

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WHAT UNWANTED REACTION WOULD BE HAPPEN DURING
ATTEMPT REDUCTION OF AND HOW MIGHT BE IT
PREVENTED?
O
O The reduction of -
OH OH
C=O is also occurred
along with -COOEt
O O
Analysis
O group. So it is
O prevented by
O O O protecting -C=O
FGI
group before
O
OH
reaction.
X OH
Synthesis O O
O OH O
O O O O CH3
O S O O O
OH OH Cl O
LiAlH4 O
H2O/H+
O
O O O
O O S CH3
OH O
O O
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SYNTHESIZE THE PARACETAMOLE BY
USING PROTECTION.

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References
Green, Protection in Organic Synthesis, 2008
Nusrat Shafiq, Role of Protective groups in Organic Synthesis, 2017
Dr. Shaikh S. Nizami , RETROSYNTHETIC APPROCH TO ORGANIC SYNTHES
PROTECTING GROUPS

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