The reagent that will effect the following selective conversion is

F1 Madhuri Teaching 16.02.2023 D49

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CSIR-UGC (NET) Chemical Science: Held on (16 Feb 2022)
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  1. NaOMe, MeOH
  2. TBAF, THF
  3. DDQ, CH2Cl2
  4. Et3N, MeOH

Answer (Detailed Solution Below)

Option 3 : DDQ, CH2Cl2
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Detailed Solution

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The correct answer is DDQ, CH2Cl2

Concept -

 –The p-Methoxybenzyl (PMB or MPM) group can be protected or deprotected under the same conditions as the benzyl group.

-PMB trichloroacetimidate (PMB-O(C=NH)CCl3) provides a way to protect base sensitive compounds under acidic conditions.

-There are two dimethoxybenzyl (DMB or DMPM) groups (2,4-dimethoxy and 3,4-dimethoxy), both of which can be deprotected under milder conditions than PMB.

Explanation

In this reaction, it is deprotected under mildly oxidizing conditions using DDQ (dichlorodicyanobenzoquinone) or strongly acidic conditions and converted to alcohol.

qImage65e023d34b6ca2bc5e724300Conclusion:-

So, The reagent that will effect the following selective conversion is DDQ, CH2Cl2.

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