Timeline for What's the mechanism of the reaction of (E)-methyl 3-(furan-2-yl)acrylate in acidic methanol?
Current License: CC BY-SA 3.0
5 events
| when toggle format | what | by | license | comment | |
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| Aug 10, 2014 at 13:12 | comment | added | Jannis Andreska | @K_P I was also sceptical about that 1,3-H shift, because of an apparent lack of "driving force" for this reaction step. Your suggested 1,5-H shift, which is driven by rearomatization and also leads to the acetal cation, makes much more sense. I have edited the mechanism accordingly. | |
| Aug 10, 2014 at 13:05 | history | edited | Jannis Andreska | CC BY-SA 3.0 |
improved mechanism according to comment
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| Aug 10, 2014 at 1:03 | comment | added | K_P | In the top part I would start by pushing electrons from the furan oxygen. That gives me the same intermediate. Then I don't really like that 1,3-H shift. You can drive forward by rearomatisation and get rid of the exocyclic double bond too, so 1,5-H shift, to give a 2-methoxyfuran which is even more reactive and will open wide by the standard mechanism, starting by pushing electrons from the furan or the methoxy O and protonate the 3-position | |
| Aug 9, 2014 at 19:14 | vote | accept | Philipp | ||
| Aug 9, 2014 at 13:57 | history | answered | Jannis Andreska | CC BY-SA 3.0 |