Pyrrole → HCID 12742325, compound

HRID 2254327Notes

Reaction equation

HRID 2254327 reaction equation
[C:1]([OH:9])(=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].ClCC(OC(=O)CCl)=O.[NH:19]1[CH:23]=[CH:22][CH:21]=[CH:20]1>ClC(Cl)C>[C:1]([C:20]1[NH:19][CH:23]=[CH:22][CH:21]=1)(=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

Participants

5

Reactant 3

HCID 8027PyrroleHCID 8094Heptanoic AcidHCID 10946Chloroacetic anhydride

Product 1

HCID 12742325HCID 12742325, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Conditions

Temperature
50 °C

Procedure

In 50 ml of dichloroethane were dissolved 6.51 g (0.05 mole) of heptanoic acid and 10.26 g (0.06 mole) of monochloroacetic anhydride. To the resulting solution were added 4.36 g (0.065 mole) of pyrrole and 0.71 g of boron trifluoride-diethyl ether complex and the resulting mixture was then stirred at 50° C. for 5.5 hours. After completion of .the reaction, the reaction solution was cooled and washed successively with water, 5% aqueous sodium carbonate solution and water. The organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure to obtain 5.74 g of 2-heptanoyl-pyrrole.

Workup

  1. customAfter completion of .the reaction
  2. temperaturethe reaction solution was cooled
  3. washwashed successively with water, 5% aqueous sodium carbonate solution and water
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b38a02a8045946ab8eae23c10bb8881b
Source dataset
uspto-grants-1993_08
Patent number
US05235068

Reaction notes

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