Diazomethane → Ethyl 4-methoxy-3-ethoxycarbonyl-1-methylpyrrole-2-acetate

HRID 1388930

Reaction equation

HRID 1388930 reaction equation
[OH:1][C:2]1[C:3]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:4]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[N:5]([CH3:7])[CH:6]=1.[N+](=[CH2:21])=[N-].CN(N=O)C(N)=O.[OH-].[K+]>C(OCC)C>[CH3:21][O:1][C:2]1[C:3]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:4]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[N:5]([CH3:7])[CH:6]=1

Participants

6

Reactant 4

HCID 9550DiazomethaneHCID 12699N-Methyl-N-nitrosoureaHCID 14797Potassium HydroxideHCID 13345719Ethyl 3-ethoxycarbonyl-4-hydroxy-1-methylpyrrole-2-acetate

Product 1

HCID 20469092Ethyl 4-methoxy-3-ethoxycarbonyl-1-methylpyrrole-2-acetate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Ethyl 4-hydroxy-3-ethoxycarbonyl-1-methylpyrrole-2-acetate (20 mmole) is dissolved in 10 μl of diethyl ether containing diazomethane freshly prepared from N-methyl-N-nitrosourea and potassium hydroxide. After the reaction is allowed to stand at room temperature for about 0.5 hour, the ether is evaporated under reduced pressure at mild temperature and the residue, i.e., crude ethyl-4-methoxy-3-ethoxycarbonyl-1-methylpyrrole-2-acetate, is used in the next step without further purification.

Workup

  1. customthe ether is evaporated under reduced pressure at mild temperature
  2. customthe residue, i.e., crude ethyl-4-methoxy-3-ethoxycarbonyl-1-methylpyrrole-2-acetate, is used in the next step without further purification

Sources & evidence

ORD record
ord-195bafe7bb434b3881f51fa3bf30cad8
Source dataset
uspto-grants-1984_02
Patent number
US04434175

Linked notes

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