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Chemistry Forums for Students => Organic Chemistry Forum => Organic Chemistry Forum for Graduate Students and Professionals => Topic started by: adam on May 13, 2008, 07:37:08 AM

Title: chemoselective in ester reduction
Post by: adam 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

Title: Re: chemoselective in ester reduction
Post by: sjb 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

Title: Re: chemoselective in ester reduction
Post by: adam 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 :)

Title: Re: chemoselective in ester reduction
Post by: sjb 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