Cyclopentanecarbonyl chloride → HCID 59576360, compound

HRID 2069508Notes

Reaction equation

HRID 2069508 reaction equation
[CH:1]1([C:6](Cl)=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.[Cl-].[Al+3].[Cl-].[Cl-].[CH2:13]([O:15][C:16]([C:18]1[NH:19][CH:20]=[CH:21][CH:22]=1)=[O:17])[CH3:14]>C(Cl)Cl>[CH2:13]([O:15][C:16]([C:18]1[NH:19][CH:20]=[C:21]([C:6]([CH:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)=[O:7])[CH:22]=1)=[O:17])[CH3:14]

Participants

5

Reactant 3

HCID 78284Cyclopentanecarbonyl chlorideHCID 255670Ethyl 1H-pyrrole-2-carboxylateHCID 6451240Aluminum(III) Chloride

Product 1

HCID 59576360HCID 59576360, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
2.5 °C

Procedure

A mixture of cyclopentanecarbonyl chloride and aluminum chloride in dry DCM were stirred in an inert atmosphere at 0-5° C. for 15 minutes. To this, a solution of 1H-pyrrole-2-carboxylic acid ethyl ester in dry DCM was added drop wise under stirring at 0-5° C., stirred further at room temperature for 4 hrs. After completion of reaction, the 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-Cyclopentanecarbonyl-1-H-pyrrole-2-carboxylic acid ethyl ester (A1-I).

Workup

  1. stirringunder stirring at 0-5° C.
  2. stirringstirred further at room temperature for 4 hrs
  3. customAfter completion of reaction
  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-f85064f160914278824ca667871fb79c
Source dataset
uspto-grants-2012_10
Patent number
US08299115B2

Reaction notes

Loading…