04-19-00 18:13
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Serious Chemistry Forum
epoxide opening
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Author Topic: epoxide opening
lexamillion
Junior Member posted 11-15-1999 07:06 PM
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new to the site but thought i would ask.
opening propylene oxide with the cuprate of 1-bromo-3,4-methylenedioxybenzene seems obvious so i'm sure it has been done before. since propylene oxide is easy to come by and (depending where you work!) so is the aryl this should give the secondary alcohol pretty easily. anyone know if there are any references for this?
appreciate feedback.
K.C. Nicolaou
Member posted 11-16-1999 12:46 AM
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Look up discussions concerning the secondary alcohol using the search engine. Most people call it MD-2-pol or some such thing. It isn't very stable, and there have been mixed(mostly bad) reports about attempts to oxidize it. If you have the grignard you are talking about, you can add DMF and obtain piperonal after hydrolysis, or you can add allyl bromide to give safrole if you want.
rev drone
Member posted 11-23-1999 11:34 AM
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I think he meant a variation of a Sn1 reaction, with HBr as a byproduct.
K.C. Nicolaou
Member posted 11-23-1999 12:18 PM
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I dunno, I thought he was saying that he wanted to brominate benzodioxole, make the cuprate from that, and treat with propylene oxide to give MD-2-pol. At least that's how I read that post. If you're still around Rev, I would appreciate a response to my question in the Chemistry forum if you would be so kind.
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