Isobutyryl chloride → HCID 59576364, compound

HRID 2069512Notes

Reaction equation

HRID 2069512 reaction equation
[C:1](Cl)(=[O:5])[CH:2]([CH3:4])[CH3:3].[Cl-].[Al+3].[Cl-].[Cl-].[CH3:11][O:12][C:13]([C:15]1[NH:16][CH:17]=[CH:18][CH:19]=1)=[O:14]>C(Cl)Cl>[CH3:11][O:12][C:13]([C:15]1[NH:16][CH:17]=[C:18]([C:1](=[O:5])[CH:2]([CH3:4])[CH3:3])[CH:19]=1)=[O:14]

Participants

5

Reactant 3

HCID 62325Isobutyryl chlorideHCID 136930Methyl pyrrole-2-carboxylateHCID 6451240Aluminum(III) Chloride

Product 1

HCID 59576364HCID 59576364, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
2.5 °C

Procedure

A mixture of isobutyryl chloride and aluminum chloride in dry DCM were stirred in an inert atmosphere at 0-5° C. for 15 minutes. To this was added a solution of 1H-pyrrole-2-carboxylic acid methyl ester in dry DCM drop wise under stirring at 0-5° C. and stirred further for 4 hours at room temperature. After completion of reaction, reaction mixture was poured into ice water and extracted with DCM, DCM layer was washed with 1N NaOH followed by water and brine. The organic layer was dried over anhydrous sodium sulfate and was evaporated to get 4-isobutyryl-1H-pyrrole-2-carboxylic acid methyl ester (B1-I)

Workup

  1. stirringunder stirring at 0-5° C.
  2. stirringstirred further for 4 hours at room temperature
  3. customAfter completion of reaction, reaction mixture
  4. extractionextracted with DCM, DCM layer
  5. washwas washed with 1N NaOH
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  7. customwas evaporated

Sources & evidence

ORD record
ord-b4ab4af19aaf4271abd9fea31f9409ce
Source dataset
uspto-grants-2012_10
Patent number
US08299115B2

Reaction notes

Loading…