Methyl 2-pyrrolecarboxylate synthesis
- Product Name:Methyl 2-pyrrolecarboxylate
- CAS Number:1193-62-0
- Molecular formula:C6H7NO2
- Molecular Weight:125.13
67-56-1
634-97-9
1193-62-0
50 mL of SOCl2 was slowly added dropwise to a solution of pyrrole-2-carboxylic acid (1) (16.65 g, 0.15 mol) dissolved in 10 mL of MeOH at 0 °C for a controlled time of 30 min. Subsequently, the reaction mixture was warmed up to 35 °C with continuous stirring for 24 hours. Upon completion of the reaction, the solvent was removed by vacuum evaporation, and the resulting residue was purified by column chromatography with the eluent being a mixed solvent of ethyl acetate/petroleum ether, which ultimately afforded Intermediate 2 as a white solid in 85% yield with a melting point of 72-73 °C.
35302-72-8
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124-41-4
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1193-62-0
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Yield:1193-62-0 95%
Reaction Conditions:
in methanol at 20; for 2 h;
Steps:
Methyl-1H-pyrrol-2-carboxylate (5)
Sodium(0.223 g, 9.7 mmol) was dissolved in dry MeOH(64 mL) at room temperature. To the resulting solution,(2-trichloroacetyl)-1H-pyrrole (14.700 g, 69.2 mmol)was added in six portions under stirring for 30 min.The reaction mixture was stirred for 2 h at room temperature(control by TLC). The solvent was evaporated,and the residue was diluted with Et2O (80 mL). To the solution, 3 M HCl (5 mL) was added, theorganic phase was separated, and the aqueous phasewas extracted with Et2O (3 × 15 mL). The combinedorganic phase was successively washed with a saturatedaqueous NaHCO3 solution and a saturatedaqueous NaCl solution and dried over Na2SO4. Thedrying agent was filtered off, and the solvent was evaporatedunder low pressure. At the next stage, the productwas used without additional purification. Ether (5)was obtained as white crystals. Yield 8.215 g (95%); Rf0.31 (PE-EtOAc 5 : 1); mp 73.0°C. The spectral characteristicscoincided with those reported in the literature[6]. 1H NMR (CDCl3): 3.86 (s, 3H), 6.26-6.28(m, 1H), 6.91-6.93 (m, 1H), 6.95-6.97 (m, 1H), 9.27(m, 1 H).
References:
Fedarkevich, A. N.;Sharko, O. L.;Shmanai, V. V. [Russian Journal of Bioorganic Chemistry,2020,vol. 46,# 2,p. 187 - 198]
67-56-1
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35302-72-8
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1193-62-0
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$5.00/1g
2133-40-6
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1193-62-0
229 suppliers
$5.00/1g
35302-72-8
172 suppliers
$10.00/5g
1193-62-0
229 suppliers
$5.00/1g