Dimethylformamide → Methyl 1-methylpyrrole-2-carboxylate

HRID 653033Notes

Reaction equation

HRID 653033 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[C:7]([OH:9])=[O:8].[CH3:10]N(C=O)C.C(N(C(C)C)C(C)C)C.CI>C(OCC)(=O)C.O>[CH3:1][N:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[C:7]([O:9][CH3:10])=[O:8]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 814531-Methyl-2-pyrrolecarboxylic acidHCID 81531Diisopropylethylamine

Product 1

HCID 142178Methyl 1-methylpyrrole-2-carboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 1-methylpyrrole-2-carboxylic acid (28.66 g., 0.229 mol) in 75 ml. DMF at 0° was added N-ethyl diisopropylamine (39.4 ml., 0.229 mol) followed by CH3I (14.27 ml., 0.229 mol). The reaction mixture was stirred 16 hours at room temperature, diluted with equal volumes each of ethyl acetate and water, the pH adjusted from 3.4 to 8.5, and the layers separated. The aqueous layer was washed 1×100 ml. fresh ethyl combined, washed 2×100 ml. H2O and 1×100 ml. brine, dried over Na2SO4 and stripped to yield title product as an oil, 24.83 g.; 1H-nmr (CDCl3) delta 3.75 (s, 3H), 3.87 (s, 3H), 5.97 (m, 1H), 6.62 (m, 1H), 6.78 (m, 1H).

Workup

  1. customthe layers separated
  2. washThe aqueous layer was washed 1×100 ml
  3. washwashed 2×100 ml
  4. dry with materialbrine, dried over Na2SO4

Sources & evidence

ORD record
ord-3c71b90a7499407db2b456dd95f71b5e
Source dataset
uspto-grants-1987_06
Patent number
US04675186

Reaction notes

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