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Topic: chemoselective in ester reduction  (Read 7451 times)

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Offline adam

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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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Offline sjb

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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 NaBH4 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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Offline adam

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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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Offline 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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