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I need help changing an epoxide into an alcohol, i.e. the second step in the scheme below. I found a reaction that created two hydroxyl groups but cannot find one that only produces one:

Epoxide to alcohol

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Superhydride (lithium triethylborohydride) does this. JACS 95 (1973) 8486 reports complete selectivity for unsubstituted over disubstituted carbon with very high yield. HC Brown JOC 45 (1980) (1) reports complete selectivity for 2-butanol from 1,2 epoxybutane and 97:3 for the reduction of styrene oxide.

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We could add grignard reagent or LiAlH4 (to conserve the carbon skeleton) to the epoxide and then protonate it.

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  • $\begingroup$ OP is not looking to make any changes to the carbon skeleton. $\endgroup$ – Zhe Jul 12 '17 at 3:09
  • $\begingroup$ @Zhe sorry, I read the ques wrongly. Maybe one could use a good H- donor such as LiAlH4 $\endgroup$ – Ayushmaan Jul 12 '17 at 3:16
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As I can say about this, we can firstly use MCPBA to form an epoxides and then by observing the product we can use Lithium Aluminum Hydride which gives hydride ion(which favours SN2 mechanism) to conserve the number of carbons in the skeleton.

And now, after this the hydride ion attaches to the less hindered site, so after that we have to do the protonation to form this product.

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