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7th August 2012 @ 03:27
Desired product obtained in 84% yield according to 1H NMR. Progressed to alkyl bromide reaction.

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Hyrdolysis of MD 1-1 (Ethyl 1-(4-fluorophenyl)-2,5-dimethyl-1H-pyrrole-3-carboxylate) to give the desired acid.

2904.gif

Reaction start time: 3:00 PM EST 7/8/12
MD 1-1 (6.5 g, 24.9 mmol, 1 equiv) was dissolved in EtOH (40 mL). 20% NaOH(aq) (40 mL, 225 mmol, 9 equiv) was added to the solution. Reaction was heated to 90°C and left over night. 10:30 AM TLC showed reaction had completed.

5 M HCL (70 mL, 350 mmol) was used to acidify the solution so that light brown crystals formed. The crystals were filtered and washed with H2O (40 mL) and EtOH (20 mL) then concentrated under reduced atmosphere to give the final product (5.04 g, 21 mmol, 84% yield).

Product characterised by 1H NMR and was used in next reaction without further purification.

TLC (25% ethyl acetate/hexane in vanilin) 8/8/12:
TLC at 10:30 AM

From left to right: MD 1-1, MD 1-1 and reaction mixture, reaction mixture.

See also:
Hydrolysis of Ethyl 1-(4-fluorophenyl)-2,5-dimethyl-1H-pyrrole-3-carboxylate (PMY 8-2)
Hydrolysis of Ethyl 1-(4-fluorophenyl)-2,5-dimethyl-1H-pyrrole-3-carboxylate (PMY 8-4)
Hydrolysis of Ethyl 1-(4-fluorophenyl)-2,5-dimethyl-1H-pyrrole-3-carboxylate (JRC 2-1)

Risk and Hazard assessment:
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Reaction
MD 2-1 Reaction.gif
TLC at 10:30 AM