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    Bugbear in the Playground
     
    HalflingPirate

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    Default Would the Grignard here only affect the epoxide?

    https://cdn.discordapp.com/attachmen...413_210414.jpg

    My eventual goal is to turn the protected oxygens into alcohols, and the oxygen in the epoxide into an oxo group.

    Ok, thought process.... Yes, only the opoxide is affected.
    The result of this reaction is close to what I'd like. I want the resulting charged oxygen to be an oxo group, and I want to turn the protected oxygens into alcohols. How can I do that?
    Last edited by MonkeySage; 2019-04-13 at 09:36 PM.
    If you run pathfinder, please check this thread out.
    http://tinyurl.com/IWJPFGR

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    Pixie in the Playground
    Join Date
    Apr 2009

    Default Re: Would the Grignard here only affect the epoxide?

    Yes the Grignard should do an Sn2-type reaction with the epoxide, and no side-reactions seem possible. There are no acidic hydrogens (Grignard reagents are strongly basic) and there are no obivous other electrophilic sites. You will get a charged oxygen species as you mention, but normally after work-up of the reaction you'd end up with the alcohol there. Turning that alcohol into an 'oxo' species or ketone will require a second reaction, with a reagent that can oxidize alcohols. Can you suggest any?

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    Bugbear in the Playground
     
    HalflingPirate

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    Default Re: Would the Grignard here only affect the epoxide?

    Ended up using swern for the ketone.
    If you run pathfinder, please check this thread out.
    http://tinyurl.com/IWJPFGR

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    Ogre in the Playground
     
    gomipile's Avatar

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    Jul 2010

    Default Re: Would the Grignard here only affect the epoxide?

    Quote Originally Posted by MonkeySage View Post
    https://cdn.discordapp.com/attachmen...413_210414.jpg

    My eventual goal is to turn the protected oxygens into alcohols, and the oxygen in the epoxide into an oxo group.

    Ok, thought process.... Yes, only the opoxide is affected.
    The result of this reaction is close to what I'd like. I want the resulting charged oxygen to be an oxo group, and I want to turn the protected oxygens into alcohols. How can I do that?
    Is opoxide a typo? If you care enough to ask the question, then why didn't you use enough care to correct a title-adjacent typo in your post?
    Quote Originally Posted by Harnel View Post
    where is the atropal? and does it have a listed LA?

  5. - Top - End - #5
    Bugbear in the Playground
     
    HalflingPirate

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    Default Re: Would the Grignard here only affect the epoxide?

    Quote Originally Posted by gomipile View Post
    Is opoxide a typo? If you care enough to ask the question, then why didn't you use enough care to correct a title-adjacent typo in your post?
    Because I didn't notice the typo until you just brought it up. It was literally one letter off.
    If you run pathfinder, please check this thread out.
    http://tinyurl.com/IWJPFGR

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