Water → Ethyl 5-(p-chlorobenzoyl)-3-ethoxycarbonyl-4-methoxy-1-methylpyrrole-2-acetate

HRID 1388919Notes

Reaction equation

HRID 1388919 reaction equation
[Cl:1][C:2]1[CH:27]=[CH:26][C:5]([C:6]([C:8]2[N:12]([CH3:13])[C:11]([CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:10]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:9]=2[OH:25])=[O:7])=[CH:4][CH:3]=1.[H-].[Na+].[CH3:30]OS(OC)(=O)=O.O>CN(C)C=O>[CH2:18]([O:17][C:15](=[O:16])[CH2:14][C:11]1[N:12]([CH3:13])[C:8]([C:6](=[O:7])[C:5]2[CH:26]=[CH:27][C:2]([Cl:1])=[CH:3][CH:4]=2)=[C:9]([O:25][CH3:30])[C:10]=1[C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH3:19]

Participants

6

Reactant 4

HCID 962WaterHCID 6497Dimethyl SulfateHCID 24758Sodium hydrideHCID 135841626Ethyl 5-(p-chlorobenzoyl)-3-ethoxycarbonyl-4-hydroxy-1-methylpyrrole-2-acetate

Product 1

HCID 20469108Ethyl 5-(p-chlorobenzoyl)-3-ethoxycarbonyl-4-methoxy-1-methylpyrrole-2-acetateYield 90.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Ethyl 5-(p-chlorobenzoyl)-3-ethoxycarbonyl-4-hydroxy-1-methylpyrrole-2-acetate (537 mg, 1.37 mmole) is added to a suspension of 70 mg of 50% sodium hydride (1.46 mmole prewashed with hexanes) in 5 ml of dry dimethylformamide (DMF) under nitrogen. After gas ceased to evolve, 150 μl of dimethylsulfate (1.57 mmole) is added all at once. The resulting yellow-orange solution is stirred for an additional 10 minutes before it is poured into 100 ml of water to precipitate the crude product. The mixture is stirred well followed by filtration. The collected residue is washed with water and dried in vacuo to afford 505 mg of crude ethyl-5-(p-chlorobenzoyl)-3-ethoxycarbonyl-4-methoxy-1-methylpyrrole-2-acetate.

Workup

  1. customto precipitate the crude product
  2. stirringThe mixture is stirred well
  3. filtrationfollowed by filtration
  4. washThe collected residue is washed with water
  5. customdried in vacuo

Sources & evidence

ORD record
ord-699918266bb2468eb178bb700890fd23
Source dataset
uspto-grants-1984_02
Patent number
US04434175

Reaction notes

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