Acetyl chloride → 4-Acetyl-1-methyl-1H-pyrrole-2-carbaldehyde

HRID 1181810Notes

Reaction equation

HRID 1181810 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[C:5](Cl)(=[O:7])[CH3:6].[CH3:9][N:10]1[CH:14]=[CH:13][CH:12]=[C:11]1[CH:15]=[O:16]>ClCCl>[C:5]([C:13]1[CH:12]=[C:11]([CH:15]=[O:16])[N:10]([CH3:9])[CH:14]=1)(=[O:7])[CH3:6]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 145041-Methyl-1H-pyrrole-2-carbaldehydeHCID 6451240Aluminum(III) Chloride

Product 1

HCID 126762684-Acetyl-1-methyl-1H-pyrrole-2-carbaldehydeYield 97.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of aluminium chloride (22.9 g, 172 mmol) in anhydrous dichloromethane (100 ml) and acetylchloride (4.5 g, 57.3 mmol)was added a solution of 1-methyl pyrrole-2-carboxaldehyde (5 g, 46 mmol) in anhydrous. dichloromethane (20 ml). The mixture was refluxed for 90 min, poured into ice and stirred until melted. The layers were separated and aqueous layer was extracted with dichloromethane (2×100 ml). The organic phase and extracts were combined, dried over sodium sulfate. The solvent was removed in vacuo to give the title compound (6.8 g, 94%), 1H NMR (d6-DMSO) d 9.6 (s, 1H), 7.9 (s, 1H), 7.4 (s, 1H), 3.9 (s, 3H),2.4 (s,3H)

Workup

  1. temperatureThe mixture was refluxed for 90 min
  2. additionpoured into ice
  3. customThe layers were separated
  4. extractionaqueous layer was extracted with dichloromethane (2×100 ml)
  5. dry with materialdried over sodium sulfate
  6. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-9a77c605ce3b4530ad35aca3a342d631
Source dataset
uspto-grants-2007_10
Patent number
US07285558B2

Reaction notes

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