Diethyl Ether → HCID 13179843, compound

HRID 1702188Notes

Reaction equation

HRID 1702188 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]1[C:8]([O:10][CH3:11])=[O:9].P(Cl)(Cl)(Cl)=O.C[CH2:18][O:19]CC.C(=O)([O-])[O-].[Na+].[Na+]>ClCCCl>[CH3:1][N:2]1[C:6]([CH:18]=[O:19])=[C:5]([CH3:7])[CH:4]=[C:3]1[C:8]([O:10][CH3:11])=[O:9]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 10340Sodium CarbonateHCID 24813Phosphorus oxychlorideHCID 13179842HCID 13179842, compound

Product 1

HCID 13179843HCID 13179843, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
90 °C

Procedure

A solution of methyl 1,4-dimethylpyrrole-2-carboxylate (2.5 g, 0.016 m) in 20 ml of dried 1,2-dichloroethane was added over two minutes to a stirred mixture of phosphorous oxychloride (2.3 ml) and dried, N,N-dimethylformamide (1.94 ml) in 50 ml of dichloroethane, and the resultant mixture heated at 90° C. (bath temperature) for 45 minutes. The cooled reaction mixture was treated with excess ice-water and ether, 10% aqueous sodium carbonate (50 ml) added, the ether layer removed and the aqueous phase re-extracted two times with fresh ether, and the combined ether layers washed well with water and dried over anhydrous sodium sulfate. Concentration of the ether solution yielded 2.48 g (84%) of methyl 1,4-dimethyl-5-formylpyrrole-2-carboxylate as a yellow solid.

Workup

  1. customdried
  2. customThe cooled reaction mixture
  3. additionadded
  4. customthe ether layer removed
  5. extractionthe aqueous phase re-extracted two times with fresh ether
  6. washthe combined ether layers washed well with water
  7. dry with materialdried over anhydrous sodium sulfate

Sources & evidence

ORD record
ord-73c9fb187a6644a68ec7ffdaf3f34f4b
Source dataset
uspto-grants-1983_04
Patent number
US04380645

Reaction notes

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