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22nd September 2011 @ 07:07
Product obtained in 65% yield.

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Scale-up of PMY 8-1 hydrolysis of Ethyl 1-(4-fluorophenyl)-2,5-dimethyl-1H-pyrrole-3-carboxylate to give the desired acid(1-(4-Fluorophenyl)-2,5-dimethyl-1H-pyrrole-3-carboxylic acid).

Reaction Scheme

Reaction start time: 16.45 EST 22/09/11
PMY 6-1 (1.05 g, 4.0 mmol, 1 equiv.) was dissolved in EtOH (approx 30 mL) and 20% NaOH (20 mL, approx 25 equiv.). Heated to reflux. After 15 hours, reaction was complete by TLC. Reaction allowed to cool to room temperature then in ice. Acidified (pH 2) with 2M HCl. Extracted with EtOAc (3 × 40 mL). Combined extracts washed with water (3 × 30 mL) and brine then dried (MgSO4) and concentrated under reduced pressure to a red/brown solid. Recrystallised (acetone/water) to give a white powder (608 mg, 65%). mpt: 241-242 °C.)

TLC (25% EtOAC/petrol) visualised with UV and vanillin:
TLC 30 minutes
TLC 15 hrs


NMR:
1H NMR
13C NMR

1H and 13C NMR


IR:
IR spectra
IR JCAMP-DX


Risk and Hazard Assessment:
As for Hydrolysis of Ethyl 1-(4-fluorophenyl)-2,5-dimethyl-1H-pyrrole-3-carboxylate (PMY 8-1)
Linked Posts
Attached Files
TLC 30 minutes
TLC 15 hrs
1H and 13C NMR
1H NMR
13C NMR
IR JCAMP-DX
IR spectra