Diethyl Ether → HCID 20464765, compound

HRID 325433Notes

Reaction equation

HRID 325433 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][CH:24]=1)[O:5][CH2:6][C:7]1[CH:8]=[C:9]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[NH:10][C:11]=1[C:12]([O:14][CH2:15][CH3:16])=[O:13].[H-].[Na+].CI.[CH3:29]COCC>CN(C=O)C.O>[CH3:29][N:10]1[C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[C:7]([CH2:6][O:5][C:4]2[CH:22]=[CH:23][CH:24]=[C:2]([CH3:1])[CH:3]=2)[CH:8]=[C:9]1[C:17]([O:19][CH2:20][CH3:21])=[O:18]

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 20464780HCID 20464780, compound

Product 1

HCID 20464765HCID 20464765, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

Diethyl 4-(3-methylphenoxy)methylpyrrole-2,5-dicarboxylate (107 g, 0.41 mol) is dissolved in dry DMF (200 ml) and added dropwise over 10 minutes to an ice-cooled suspension of hexanes-washed sodium hydride (0.41 mol) in dry DMF (400 ml). The resulting mixture was then stirred for one hour, then recooled in an ice bath and treated dropwise over 15 minutes with methyl iodide (30 ml, 0.49 mol). Stirring is continued for an additional thirty minutes, then the mixture is slowly poured into a separatory funnel containing ether (500 ml) and water (one liter). The ether layer was washed with water and saturated brine, then dried over sodium sulfate and the solvent removed in vacuo to give diethyl 1-methyl-4-(3-methylphenoxy)methylpyrrole-2,5-dicarboxylate.

Workup

  1. temperaturecooled
  2. customrecooled in an ice bath
  3. stirringStirring
  4. waitis continued for an additional thirty minutes
  5. additionthe mixture is slowly poured into a separatory funnel
  6. washThe ether layer was washed with water and saturated brine
  7. dry with materialdried over sodium sulfate
  8. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-a65ea7fd5d9c414c95066d91c5a399a9
Source dataset
uspto-grants-1984_04
Patent number
US04440779

Reaction notes

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