1-Methyl-1H-pyrrole-2-carbaldehyde → HCID 20110104, compound

HRID 1181811Notes

Reaction equation

HRID 1181811 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[C:5](Cl)(=[O:8])[CH2:6][CH3:7].[CH3:10][N:11]1[CH:15]=[CH:14][CH:13]=[C:12]1[CH:16]=[O:17]>ClCCl>[CH3:10][N:11]1[CH:15]=[C:14]([C:5](=[O:8])[CH2:6][CH3:7])[CH:13]=[C:12]1[CH:16]=[O:17]

Participants

5

Reactant 3

HCID 145041-Methyl-1H-pyrrole-2-carbaldehydeHCID 62324Propionyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 20110104HCID 20110104, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of aluminium chloride (22.9 g, 172 mmol) in anhydrous dichloromethane (100 ml) and propionylchloride (5.3 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 (7.2 g, 95%), 1H NMR (d6-DMSO) d 9.6 (s, 1H), 7.9 (s, 1H), 7.4 (s, 1H), 3.9 (s, 3H), 2.8 (q, 2H), 1.06 (t, 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-72ca781fece34fd2b9fb9e6c28db9ba3
Source dataset
uspto-grants-2007_10
Patent number
US07285558B2

Reaction notes

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