[ricecake]

This is part of a reaction chain:
Pyrrole + CH₃MgBr  A + C₂H₅I    B + t°  C + KOH  D

This is what I got so far:
A is
B is
I got stuck at C. Would the ring just pop open because of the heat?

[orgopete]

This looks like a case of the missing reactant. I don't think you can quaternize pyrrole like that. Okay for an N-alkylation. Heating B makes more sense if a dienophile were present. Then reacting with KOH with its functionality would seem more plausible. I'm just guessing though.

[ricecake]

This looks like a case of the missing reactant. I don't think you can quaternize pyrrole like that. Okay for an N-alkylation. Heating B makes more sense if a dienophile were present. Then reacting with KOH with its functionality would seem more plausible. I'm just guessing though.

I was following the Hoffmann elimination reaction for a simple cyclic nitrogen...I tried to google reactions for pyrrole but not much coming up. Should I look at some specific sites?

[orgopete]

If this is a problem covered in a class or textbook, I missed that class. I was simply guessing. You could give us more information or tell me I'm wrong. Can anyone else solve this?

[discodermolide]

According to literature http://pubs.acs.org/doi/abs/10.1021/jo01013a008?journalCode=joceah  the pyrrole Grignard reagent gives a mixture of products with chlorobutyronitrile:


and


with the 2-substituted product the major one.
See where you can go from there?

[ricecake]

If this is a problem covered in a class or textbook, I missed that class. I was simply guessing. You could give us more information or tell me I'm wrong. Can anyone else solve this?

No sorry  I didn't mean to say that you were incorrect or anything. I just wanted to tell you where I got my information https://books.google.com/books?id=7quC1QxHAG0C&pg=PA74&lpg=PA74&dq=Pyrrole+%2B+CH3MgBr&source=bl&ots=Gb497HVFE0&sig=uJM_WM_o9S-kFywiSSbUs--OYbg&hl=en&sa=X&ei=eZ-sVIGNEc6OyAS0yIHwCg&ved=0CCQQ6AEwAQ#v=onepage&q=Pyrrole%20%2B%20CH3MgBr&f=false