ORGLIST: Re: Everybody Digest, Vol 12, Issue 19

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From: Lakshmipathi Pandarinathan (plpathi$##$hotmail.com)
Date: Wed Sep 28 2005 - 17:20:34 EDT


Tuyen
I am sorry for the earlier message with suggestion to use BF3 and thiol
method and I think you might have the addition product?! Actually I used
FeCl3 in a very similar situation where in I had conjugated double bond and
I got the desired product with low yields (10%). Fraser-Reid's paper on
benzyl ether cleavage details the use of very anhydrous FeCl3 for this
purpose. However, freshly opened FeCl3 also gave low yields. I even tried
using FeCl3 impregnated on silica gel, but no product was formed. I feel
that by using very anhydrous FeCl3, you could get the product albeit
moderate yields.
Pathi

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Subject: Everybody Digest, Vol 12, Issue 19


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> 1. benzyl deprotection (truong tuyen)
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> Message: 1
> Date: Tue, 27 Sep 2005 20:53:30 -0700 (PDT)
> From: truong tuyen <truongtuyen2001$##$yahoo.com>
> Subject: ORGLIST: benzyl deprotection
> To: everybody$##$orglist.net
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> Hello,
>
> Can anyone suggest a method for benzyl deprotection (benzyloxy attached
> with phenyl group) without affecting methoxy group (MeO-) and conjugated
> double bond.
> I tried with FeCl3/CH2Cl2 at room temperature, Li/naphthalene/ - 25
> degree, but I could not get desired product.
> Please help me,
> Thanks in advance.
>
>
> Tuyen
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