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19th August 2011 @ 03:28
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See also:

Paal-Knorr Synthesis of 1-aryl-2,5-dimethyl Pyrrole Core (PMY 1-3)
Paal-Knorr Synthesis of 1-aryl-2,5-dimethyl Pyrrole Core (PMY 1-2)
Paal-Knorr Synthesis of 1-aryl-2,5-dimethyl Pyrrole Core (PMY 1-1)


Reaction Scheme PY14.png

Experiment start time: 9.46 EST 19/08/2011
4-fluoroaniline (312 μL, 3.3 mmol, 1.1 equiv.) and 2,5-hexanedione (352 μL, 3 mmol, 1 equiv.) were heated to 130 °C (oil bath temp.). 5 hours, then cooled. Dissolved in diethyl ether (20 mL) and washed with 10% citric acid (2 × 5 mL), dried (MgSO4) and concentrated under reduced pressure to a brown oil (439 mg). TLC shows removal of aniline. Solidified into needles and brown solid (0830 EST 22/08/11). 1H NMR consistant with product, and Et2O (approx. 77:23).

TLC (10% EtOAc/petrol) visualised with UV and vanillin:
Washed product TLC
4-fluoroaniline (left), mixed (middle), citric acid washed PMY 1-4 (right).

1H NMR Spectra:
crude NMR


Hazard and Risk Assessment
As for Paal-Knorr Synthesis of 1-aryl-2,5-dimethyl Pyrrole Core (PMY 1-2), except reaction carried out neat.
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TLCpostwash
TLCpostwash
ReactionScheme
crude NMR