Ethyl orthoformate → ethyl 5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxylate

HRID 2252156Notes

Reaction equation

HRID 2252156 reaction equation
C([O:5][C:6]([C:8]1[NH:9][C:10]([CH3:19])=[C:11]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:12]=1[CH3:13])=O)(C)(C)C.C(OCC)(OCC)OCC>FC(F)(F)C(O)=O>[CH3:19][C:10]1[NH:9][C:8]([CH:6]=[O:5])=[C:12]([CH3:13])[C:11]=1[C:14]([O:16][CH2:17][CH3:18])=[O:15]

Participants

4

Reactant 2

HCID 31214Ethyl orthoformateHCID 43476602-Tert-butyl 4-ethyl 3,5-dimethyl-1h-pyrrole-2,4-dicarboxylate

Product 1

HCID 137485ethyl 5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxylateYield 64%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
15 °C

Procedure

A mixture of 2-tert-butyloxycarbonyl-3,5-dimethyl-4-ethoxycarbonylpyrrole and triethyl orthoformate (1.5 equiv.) in trifluoroacetic acid was stirred at 15° C. for 1 hour. The reaction was concentrated and the residue was purified to give (64%) 2,4-dimethyl-3-ethoxycarbonyl-5-formylpyrrole as yellow needles.

Workup

  1. concentrationThe reaction was concentrated
  2. customthe residue was purified

Sources & evidence

ORD record
ord-91bd38caaebe4e2fa182873e4bc3e50f
Source dataset
uspto-grants-2008_01
Patent number
US07320996B2

Reaction notes

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