Ethanol → Ethyl 4-phenyl-1H-pyrrole-2-carboxylate

反応式

[Na].Cl.[CH3:3][O:4][C:5](=[O:8])[CH2:6][NH2:7].Cl([O-])(=O)(=O)=O.CN(C)[CH:16]=[C:17]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH:18]=[N+](C)C.[CH2:29](O)C>>[C:22]1([C:17]2[CH:16]=[C:6]([C:5]([O:4][CH2:3][CH3:29])=[O:8])[NH:7][CH:18]=2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

参加物

反応物 4

HCID 702Ethanol

HCID 122755Glycine methyl ester hydrochloride

HCID 5360545Sodium

HCID 78294239(3-Dimethylamino-2-phenyl-prop-2-enylidene)-dimethyl-ammonium perchlorate

生成物 1

HCID 14643813Ethyl 4-phenyl-1H-pyrrole-2-carboxylate収率 57%

実験手順

Sodium metal (900 mg, 41.0 mmol) was added to dry ethanol (150 mL) and allowed to dissolve over 30 min. Glycine methyl ester hydrochloride (3.2 g, 25.0 mmol) and (3-dimethylamino-2-phenyl-prop-2-enylidene)-dimethyl-ammonium perchlorate (5.0 g, 16.0 mmol) were added successively and the reaction mixture heated at reflux for 16 h. Ethanol was evaporated in vacuo, the residue diluted with water and extracted with chloroform. The organic layer was washed with water, brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The crude product obtained was purified by column chromatography over neutral alumina using 10% ethyl acetate in petroleum ether as eluent to afford ethyl 4-phenyl-1H-pyrrole-2-carboxylate (2.0 g, 57%) as a solid.