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chemoselective in ester reduction
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Topic: chemoselective in ester reduction (Read 7442 times)
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adam
Regular Member
Posts: 28
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chemoselective in ester reduction
«
on:
May 13, 2008, 07:37:08 AM »
Hi, I want to reduce an epoxy ester to epoxyalcohol...any idea to reduce selectively the ester and not open the epoxide?
The epoxide contains a bencilic carbon (so reactive)
Thanks
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sjb
Global Moderator
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Re: chemoselective in ester reduction
«
Reply #1 on:
May 13, 2008, 07:57:51 AM »
What sort of relationship is there between your epoxide and ester?
Quick NaBH
4
reduction? (
http://dx.doi.org/10.1039/C39860000395
)
Is there anything in
http://dx.doi.org/10.1039/CS9760500023
of use?
S
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adam
Regular Member
Posts: 28
Mole Snacks: +1/-1
Re: chemoselective in ester reduction
«
Reply #2 on:
May 21, 2008, 12:22:43 PM »
Thanks sjb! was very useful
The reduction works using a large excess of NaBH4 in EtOH and heating a little bit
. The epoxide remains unaffected
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sjb
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Re: chemoselective in ester reduction
«
Reply #3 on:
May 22, 2008, 12:01:32 PM »
Really? That's good to know! What sort of scale did you do it on and how much of an excess of borohydride? (Just to mentally file away for future reference)
S
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chemoselective in ester reduction