Dimethylformamide → 5-Methyl-3-(propan-2-yl)-1H-pyrrole-2-carbaldehyde

HRID 1828894Notes

Reaction equation

HRID 1828894 reaction equation
CN([CH:4]=[O:5])C.O=P(Cl)(Cl)Cl.[CH:11]([C:14]1[CH:18]=[C:17]([CH3:19])[NH:16][CH:15]=1)([CH3:13])[CH3:12].[OH-].[Na+]>ClC(Cl)C.O>[CH:11]([C:14]1[CH:18]=[C:17]([CH3:19])[NH:16][C:15]=1[CH:4]=[O:5])([CH3:13])[CH3:12]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 22059886HCID 22059886, compound

Product 1

HCID 220592415-Methyl-3-(propan-2-yl)-1H-pyrrole-2-carbaldehydeYield 67%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 63651,1-DichloroethaneSolvent2×

Procedure

To a solution of anhydrous DMF (2.1 ml, 27 mmol) in anhydrous dichloroethane (50 ml) at 0° C. under nitrogen, POCl3 (2.1 ml, 23 mmol) was added dropwise. The solution was allowed to warm at room temperature for 1 h. Then, the suspension was cooled at 0° C. and a solution of 3-isopropyl-5-methylpyrrole (2 g, 16 mmol) in dichloroethane (20 ml) was added dropwise over 20 min. After stirring at room temperature for 24 h, water followed by NaOH were added to pH: 8. The organic layer was extracted, dried and the solvent removed to dryness. The residue was purified by flash chromatography. Yield 67%, m.p. 90–93° C.

Workup

  1. temperatureThen, the suspension was cooled at 0° C.
  2. additionwere added to pH: 8
  3. extractionThe organic layer was extracted
  4. customdried
  5. customthe solvent removed to dryness
  6. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-616fe5dc6f4b45529faa580385fed4d3
Source dataset
uspto-grants-2006_06
Patent number
US07060822B1

Reaction notes

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