Acetic Acid → Ethyl 3-sec-butyl-5-methyl-1H-pyrrole-2-carboxylate

HRID 1967416Notes

Reaction equation

HRID 1967416 reaction equation
C([O-])(=O)C.[NH4+].C(O)(=O)C.O[N:11]=[C:12]([CH:18]([CH2:23][C:24](=O)[CH3:25])[CH:19]([CH3:22])[CH2:20][CH3:21])[C:13]([O:15][CH2:16][CH3:17])=[O:14]>O>[CH:19]([C:18]1[CH:23]=[C:24]([CH3:25])[NH:11][C:12]=1[C:13]([O:15][CH2:16][CH3:17])=[O:14])([CH2:20][CH3:21])[CH3:22]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 517165Ammonium AcetateHCID 86642082Ethyl 2-(hydroxyimino)-4-methyl-3-(2-oxopropyl)hexanoate

Product 1

HCID 68528573Ethyl 3-sec-butyl-5-methyl-1H-pyrrole-2-carboxylate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

Ammonium acetate (92.5 g) was added to the acetic acid solution (430 mL) of the compound prepared in Example 16 under argon gas atmosphere. The reaction mixture was stirred at 100° C. for an hour. Water was added to the reaction mixture, and the reaction mixture was stirred for an hour. A precipitate was filtrated. The precipitate which was filtrated was dissolved in methylene chloride again, and the solution was purified by column chromatography on silica gel (ethyl acetate:n-hexane=1:3) to obtain a title compound (44.1 g) having the following physical data.

Workup

  1. stirringthe reaction mixture was stirred for an hour
  2. filtrationA precipitate was filtrated
  3. filtrationThe precipitate which was filtrated
  4. dissolutionwas dissolved in methylene chloride again
  5. customthe solution was purified by column chromatography on silica gel (ethyl acetate:n-hexane=1:3)

Sources & evidence

ORD record
ord-ad94c0b2ab484603aceba3220323d494
Source dataset
uspto-grants-2013_04
Patent number
US08420810B2

Reaction notes

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