Diethyl Ether → HCID 13179851, compound

HRID 1702190Notes

Reaction equation

HRID 1702190 reaction equation
[CH3:1][C:2]1[CH:6]=[C:5]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[NH:4][C:3]=1[C:12]([O:14][CH2:15][CH3:16])=[O:13].[H-].[Na+].[CH3:19]CCCCC.CI.CCOCC>CN(C)C=O.O>[CH3:19][N:4]1[C:5]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:6][C:2]([CH3:1])=[C:3]1[C:12]([O:14][CH2:15][CH3:16])=[O:13]

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 6328Methyl iodideHCID 584426Diethyl 3-methyl-1H-pyrrole-2,5-dicarboxylateHCID 86738843HCID 86738843, compound

Product 1

HCID 13179851HCID 13179851, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

The diethyl 3-methylpyrrole-2,5-dicarboxylate obtained in Step A was taken up in dried N,N-dimethylformamide (100 ml) and added dropwise over 10 minutes, under nitrogen to an ice-cooled suspension of washed (hexane) sodium hydride (from 16.2 g, 0.41 m of 60% sodium hydride in mineral oil dispersion) in dried N,N-dimethylformamide (400 ml). The resulting mixture was then stirred without cooling for 1 hour, recooled in an ice-bath and treated dropwise over ca. 15 minutes with methyl iodide (30.3 ml, 0.49 m). After stirring for an additional 30 minutes, the mixture was slowly poured into a separatory funnel containing ether (0.5 liter) and water (1 liter). The separated ether layer was washed with water and saturated sodium chloride solution, dried, and concentrated to a tan solid. Purification via chromatography (silica gel/hexane-EtOAc) yielded diethyl 1,3-dimethylpyrrole-2,5-dicarboxylate (75 g) as a white solid, m.p. 48°-48.5° C.

Workup

  1. temperaturecooled
  2. temperaturewithout cooling for 1 hour
  3. customrecooled in an ice-bath
  4. stirringAfter stirring for an additional 30 minutes
  5. additionthe mixture was slowly poured into a separatory funnel
  6. washThe separated ether layer was washed with water and saturated sodium chloride solution
  7. customdried
  8. concentrationconcentrated to a tan solid
  9. customPurification via chromatography (silica gel/hexane-EtOAc)

Sources & evidence

ORD record
ord-cc62a21c2c1446228591553433d2d29e
Source dataset
uspto-grants-1983_04
Patent number
US04380645

Reaction notes

Loading…