Ceric ammonium nitrate → 2-formyl-1-isopropyl-1H-pyrrole-3-carboxylic acid ethyl ester

HRID 2204295Notes

Reaction equation

HRID 2204295 reaction equation
O=[N+]([O-])[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-:21][N+](=O)[O-].[Ce+4].[NH4+].[NH4+].[CH2:28]([O:30][C:31]([C:33]1[CH:37]=[CH:36][N:35]([CH:38]([CH3:40])[CH3:39])[C:34]=1[CH3:41])=[O:32])[CH3:29]>CC#N.O>[CH2:28]([O:30][C:31]([C:33]1[CH:37]=[CH:36][N:35]([CH:38]([CH3:40])[CH3:39])[C:34]=1[CH:41]=[O:21])=[O:32])[CH3:29]

Participants

5

Reactant 2

HCID 180504Ceric ammonium nitrateHCID 215837461-isopropyl-2-methyl-1H-pyrrole-3-carboxylic acid ethyl ester

Product 1

HCID 867030972-formyl-1-isopropyl-1H-pyrrole-3-carboxylic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

CAN (979 mmol) was added to a mixture of 1-isopropyl-2-methyl-1H-pyrrole-3-carboxylic acid ethyl ester [224180-70-5] (218 mmol) in CH3CN (1800 mL) and water (360 mL) at 15° C. After 10 min, the reaction mixture was quenched with ice and extracted with MTBE. The organic phase was successively washed with a saturated aqueous solution of NaHCO3 (2×) and brine, dried (Na2SO4), filtered and concentrated. The residue was purified by silica gel column chromatography to afford the title compound as a yellow oil. tR: 4.43 min (HPLC 1); ESI-MS: tR=1.06 min, [M+H]+ 210 (LC-MS 1); TLC: Rf=0.21 (1:9 EtOAc/heptanes).

Workup

  1. customthe reaction mixture was quenched with ice
  2. extractionextracted with MTBE
  3. washThe organic phase was successively washed with a saturated aqueous solution of NaHCO3 (2×) and brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-186122ef40df4e51801220e777b6d629
Source dataset
uspto-grants-2016_06
Patent number
US09365576B2

Reaction notes

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