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How can I make the product in the picture below from cyclohexanone? I did Stork enamine synthesis, but it results in terminal primary alcohol. I need secondary alcohol with one more carbon atom at end. How to do that?

2-(3-hydroxybutyl)cyclohexan-1-ol

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    $\begingroup$ How about a Michael addition of the cyclohexanone enolate to methyl vinyl ketone; follow this with a reduction of both carbonyls. $\endgroup$ – ron Mar 21 '16 at 21:17
  • $\begingroup$ @ron How do you prevent Robinson annulation? $\endgroup$ – Loong Mar 22 '16 at 11:05
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    $\begingroup$ @Loong Good point, so you'd use an enamine (like the OP suggested) instead of the enolate and run the Michael addition under neutral conditions. $\endgroup$ – ron Mar 22 '16 at 14:13

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