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11th January 2012 @ 07:40
Acetylation of para-methyl arylpyrrole near neighbour analogue


Experiment start time: 5:15 EST 11/01/2012
ZYH 5-1 (50 mg, 0.13 mmol, 1 equiv.) was dissolved partially in toluene (~5 mL) and stirred under a nitrogen atmosphere. Pyridine (~20 μL, 0.25 mmol, 1.9 equiv.) was added, followed by acetic anhydride (~40 μL, 0.4 mmol, 3 equiv.). The mixture was heated to 80 °C and left stirring overnight under nitrogen. In the morning the mixture was evaporated under reduced pressure to give a yellow powder and monitored by H NMR, which showed complete disappearance of starting materials but the presence of some impurities. The powder was dissolved in ethyl acetate and adsorbed onto silica and washed with hexane (~ 150 mL) then washed off the silica with ethyl acetate and concentrated under reduced pressure to return a yellow powder (25 mg, 54%). Some mass was lost and appeared to have been retained on the silica but the product was relatively clean by H NMR.

Data summary table:
Yield % Melting point °C 1H NMR 13C NMR19F NMR IR Mass spec
ZYH 17-1 54 decomposes ~256Impurities (pdf May need resynthesisNAYes (pdf, .dx) Submitted for APCI

Hazard and risk assessment:
Refer to: Acetylation of para-trifluoromethyl near neighbour analogue (ZYH 12-1)
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reaction scheme
IR data
IR spectrum
1H NMR initial