Dimethylformamide → Ethyl 5-formyl-4-methyl-1H-pyrrole-2-carboxylate

HRID 1072130Notes

Reaction equation

HRID 1072130 reaction equation
P(Cl)(Cl)(Cl)=O.[CH2:6]([O:8][C:9]([C:11]1[NH:12][CH:13]=[C:14]([CH3:16])[CH:15]=1)=[O:10])[CH3:7].[OH-].[Na+].CN(C)[CH:21]=[O:22]>O>[CH2:6]([O:8][C:9]([C:11]1[NH:12][C:13]([CH:21]=[O:22])=[C:14]([CH3:16])[CH:15]=1)=[O:10])[CH3:7]

Participants

6

Reactant 4

HCID 6228Dimethylformamide2×HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 643361Ethyl 4-methyl-1H-pyrrole-2-carboxylate

Product 1

HCID 9855648Ethyl 5-formyl-4-methyl-1H-pyrrole-2-carboxylateYield 68%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To ice-cold 3 mL (39.2 mmol) of N,N-dimethylformamide (DMF) was added phosphorus oxychloride (0.67 mL, 7.18 mmol) dropwise and the resultant mixture was stirred for 30 minutes. A solution of 1 g (6.53 mmol) of 4-methyl-1H-pyrrole-2-carboxylic acid ethyl ester in 3 mL of DMF was added to the reaction. After 1 hour, the reaction was warmed to room temperature for another 2.5 hours. The reaction mixture was diluted with water (100 mL) and basified to pH=11 with 1N sodium hydroxide solution. The precipitate was removed by filtration, rinsing with water and dried to afford 0.8 g (68%) of 5-formyl-4-methyl-1H-pyrrole-2-carboxylic acid ethyl ester as a white solid. 1H NMR (360 MHz, DMSO-d6) d 12.6 (br s, 1H, NH), 9.78 (s, 1H, CHO), 6.68 (s, 1H), 4.26 (q, J=7.0 Hz, 2H, OCH2CH3), 2.28 (s, 3H, CH3), 1.28 (t, J=7.0 Hz, 3H, OCH2CH3). MS 181 [M+].

Workup

  1. customThe precipitate was removed by filtration
  2. washrinsing with water
  3. customdried

Sources & evidence

ORD record
ord-0001563f291844f59f2ca2c9f49de830
Source dataset
uspto-grants-2005_06
Patent number
US06908930B2

Reaction notes

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