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24th October 2012 @ 03:52
Product obtained in 64% yield.

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Hydrolysis of PMY 58-2 methyl ester to the acid using aqueous sodium hydroxide.

PMY59-1.png

Reaction Start Time: 12.30 24/10/12
PMY 58-3 (240 mg, 0.76 mmol, 1 equiv.) was dissolved in hot methanol (15 mL). 5M NaOH(aq) (4 mL) was added and the reaction stirred at room temperature. After 2 hours, reaction not complete. 3 pellets of NaOH added and the mixture heated to reflux briefly then cooled. After 30 minutes, reaction complete. The mixture was acidified using 6M HCl and cooled in a salt/ice bath. Pale yellow needle crystals form. Filtered and washed with water then dried (146 mg, 64%).

TLC (5% MeOH/DCM) visualised with UV and vanillin:
TLC


NMR:
1H NMR


See also:
Cyclodehydration of carboxamide PMY 67-1 (PMY 58-3)
Hydrolysis of PMY 58-2 methyl ester (PMY 59-2)

Risk and Hazard Assessment:
As for Hydrolysis of Ethyl 1-(4-fluorophenyl)-2,5-dimethyl-1H-pyrrole-3-carboxylate (PMY 8-2)
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