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31st July 2012 @ 00:21
Product obtained (1H NMR evidence only) in 52% yield. Used without further purification.

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

PMY59-1.png

Reaction start time: 13.40 30/07/12
PMY 58-2 (126 mg, 0.4 mmol, 1 equiv.) was stirred in MeOH (5 mL). Partial solution, yellow solution, some white crystals. Sodium hydroxide (160 mg, 4.0 mmol, 10 equiv.) was dissolved in water (2 mL) and added to the solution of PMY 58-2. After 1.5 hours, the reaction was mostly complete by TLC. 2M HCl(aq) was added until pH 1. The mixture was then extracted with DCM (3 × 5 mL). The organic extracts were washed with brine then dried (MgSO4) and concentrated to a yellow solid (62 mg). 1H NMR consistent with product. Some further crystals precipitate from aqueous, further extraction required. Material used without further purification.

TLC (50% acetone/hexane) visualised with UV and vanillin:
TLC 1.5 hours
TLC 1 hour


NMR:
1H NMR


See also:
Scaled-up cyclodehydration of carboxamide PMY 57-2 (PMY 58-2)
Hydrolysis of ethyl 5-methyl-1-phenyl-1H-pyrazole-4-carboxylate (PMY 44-1)
Hydrolysis of Ethyl 1-(4-fluorophenyl)-2,5-dimethyl-1H-pyrrole-3-carboxylate (JRC 2-1)
Hydrolysis of Ethyl 1-(4-fluorophenyl)-2,5-dimethyl-1H-pyrrole-3-carboxylate (PMY 8-2)

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

[Reaction reporting delayed to 31/07/12 due to server error]
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Scheme
TLC 1 hour
TLC 1.5 hours
1H NMR
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