Dimethylformamide → Methyl 1-methylpyrrole-2-carboxylate

HRID 34734

Reaction equation

HRID 34734 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 evaporated. 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 evaporated
  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-8846fd4203b048b2955171644a99b630
Source dataset
uspto-grants-1988_08
Patent number
US04762921

Linked notes

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