ChemicalBook CAS DataBase List Ethyl 2,4-dimethyl-1H-pyrrole-3-carboxylate

Ethyl 2,4-dimethyl-1H-pyrrole-3-carboxylate synthesis

7synthesis methods

Product Name:Ethyl 2,4-dimethyl-1H-pyrrole-3-carboxylate
CAS Number:2199-51-1
Molecular formula:C9H13NO2
Molecular Weight:167.21

3,5-Dimethylpyrrole-2,4-dicarboxylic acid 2-t-butyl ester-4-ethyl ester

86770-31-2

Ethyl 2,4-dimethyl-1H-pyrrole-3-carboxylate

2199-51-1

Step (ii): Preparation of 2,4-dimethyl-1H-pyrrole-3-carboxylic acid ethyl ester In a 10-liter four-necked round-bottomed flask equipped with a mechanical stirrer, thermometer casing, gas introduction tube, and air condenser, 3,5-dimethyl-1H-pyrrole-2,4-dicarboxylic acid 2-tert-butyl ester 4-ethyl ester (II) (1.5 kg, 5.6 mol) and isopropanol (4.5 L) were added and stirred at 25-30 °C. Concentrated hydrochloric acid (2.2 L) was added slowly through the addition funnel. After addition, the reaction mixture was warmed up to 45-50 °C and maintained at this temperature until complete cessation of gas release. The reaction progress was monitored by thin layer chromatography (TLC). Upon completion of the reaction, the solution was cooled to 25-30 °C and quenched in an ice-water bath. The product was separated by filtration and dried at 50 °C. A dried product of 721.3 g was obtained with 77.3% yield and >96% HPLC purity.

4-(Ethoxycarbonyl)-3,5-dimethyl-1H-pyrrole-2-carboxylic acid

5442-91-1
117 suppliers
$25.00/500mg

2199-51-1
247 suppliers
$7.00/250mg

Yield:2199-51-1 98.5%

Reaction Conditions:

Inert atmosphere;Temperature;

Steps:

Ethyl 2,4-dimethyl-1H-pyrrole-3-carboxylate (8)
4-(Ethoxycarbonyl)-3,5-dimethyl-1H-pyrrole-2-carboxylic acid (7, 5.0 g, 25.0 mmol) was heated in a flask to 200-210 °C with an oil bath for 12 min. The reactant gradually melted with accompanying production of carbon dioxide. The heating was removed when there was no more gas evolving. The reaction was allowed to cool down to r.t. and then dried under vacuum to afford 8 as a pale-gray solid (3.90 g, 98.5 %), m.p. 75-76 °C (lit. 74-76 °C [17]), yield 90.0 % (lit. [13]). R_f = 0.73 (eluent: chloroform/methanol, v/v = 10:1).

References:

Meng, Ge;Liu, Chunyan;Qin, Shidong;Dong, Mengshu;Wei, Xiaomi;Zheng, Meilin;Qin, Liwen;Wang, Huihui;He, Xiaoshuang;Zhang, Zhiguo [Research on Chemical Intermediates,2015,vol. 41,# 11,p. 8941 - 8954]

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86770-31-2
154 suppliers
$19.78/1gm:

2199-51-1
247 suppliers
$7.00/250mg

References