Methane, dichloromethoxy- → Methyl 4-formyl-1-methyl-1H-pyrrole-2-carboxylate

HRID 1702187Notes

Reaction equation

HRID 1702187 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[C:7]([O:9][CH3:10])=[O:8].[Cl-].[Al+3].[Cl-].[Cl-].Cl[CH:16]([O:18]C)Cl>ClCCCl.[N+](C)([O-])=O>[CH:16]([C:5]1[CH:4]=[C:3]([C:7]([O:9][CH3:10])=[O:8])[N:2]([CH3:1])[CH:6]=1)=[O:18]

Participants

6

Reactant 3

HCID 21004Methane, dichloromethoxy-HCID 142178Methyl 1-methylpyrrole-2-carboxylateHCID 6451240Aluminum(III) Chloride

Product 1

HCID 2798349Methyl 4-formyl-1-methyl-1H-pyrrole-2-carboxylate

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolvent2×HCID 6375NitromethaneSolvent

Procedure

To a mixture of methyl 1-methylpyrrole-2-carboxylate (5.0 g, 0.036 m) and 11.4 g anhydrous aluminum chloride in 150 ml of 1:1 1,2-dichloroethane and nitromethane at -20° C. was added over two minutes a solution of dichloromethyl methylether (3.9 ml, 0.043 m) in 1,2-dichloroethane (20 ml). The resultant mixture was stirred at -10° to -30° C. for 3 hours, quenched with excess ice-water, the resultant mixture extracted well with ether, and the combined ether extracts washed two times with water, passed through a small layer of sodium sulfate-silica gel, and concentrated in vacuo to 5.4 g (90%) of methyl 4-formyl-1-methylpyrrole-2-carboxylate, m.p. 95°-97° C.

Workup

  1. customquenched with excess ice-water
  2. extractionthe resultant mixture extracted well with ether
  3. washthe combined ether extracts washed two times with water
  4. concentrationconcentrated in vacuo to 5.4 g (90%) of methyl 4-formyl-1-methylpyrrole-2-carboxylate, m.p. 95°-97° C.

Sources & evidence

ORD record
ord-f70928cf2ec542239cda036921bee409
Source dataset
uspto-grants-1983_04
Patent number
US04380645

Reaction notes

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