Acetic Acid → diethyl 1H-pyrrole-2,5-dicarboxylate

HRID 1796643

Reaction equation

HRID 1796643 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]([CH:11]=[O:12])=[CH:9][CH:10]=1)=[O:5])[CH3:2].[C-]#N.[K+].[CH3:16][C:17](O)=[O:18]>CCO.O=[Mn]=O>[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]([C:11]([O:18][CH2:17][CH3:16])=[O:12])=[CH:9][CH:10]=1)=[O:5])[CH3:2]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 9032Potassium CyanideHCID 321485ethyl 5-formyl-1H-pyrrole-2-carboxylate

Product 1

HCID 21025083diethyl 1H-pyrrole-2,5-dicarboxylateYield 76.7%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 702EthanolSolvent

Procedure

To a mixture of 406A (167 mg, 1.0 mmol), KCN (325.6 mg, 5.0 mmol) in anhydrous EtOH (20 ml) was added AcOH (85.9 μl, 1.5 mmol) followed by activated MnO2 (1.643 g, 20 mmol). The reaction was stirred overnight. After workup, the residue was purified by silica gel flash column chromatography to give 406B (162 mg, 77%) as a pinkish solid (25% EtOAc—hexanes).

Workup

  1. customAfter workup, the residue was purified by silica gel flash column chromatography

Sources & evidence

ORD record
ord-73c257903a4e4b13ab81a84fd824f0af
Source dataset
uspto-grants-2006_04
Patent number
US07030112B2

Linked notes

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