Dimethylformamide → Methyl pyrrole-2-carboxylate

HRID 653034Notes

Reaction equation

HRID 653034 reaction equation
[NH:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([OH:8])=[O:7].[CH3:9]N(C=O)C.C(N(C(C)C)C(C)C)C.CI>O.C(OCC)(=O)C>[NH:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([O:8][CH3:9])=[O:7]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 12473Pyrrole-2-Carboxylic AcidHCID 81531Diisopropylethylamine

Product 1

HCID 136930Methyl pyrrole-2-carboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To pyrrole-2-carboxylic acid (1.11 g., 0.010 mol) in 5 ml. DMF at 0° was added N-(ethyl)diisopropylamine (1.806 ml., 0.0105 mol) followed by methyl iodide (0.654 ml., 0.0105 mol). The mixture was stirred 18 hours at room temperature, diluted with 10 ml. ethyl acetate and 10 ml. H2O, the pH adjusted to 8.5, and the organic layer separated, washed 1×10 ml. H2O, dried over Na2SO4, and stripped with CHCl3 chase to yield title product as a gummy solid containing 10% DMF, 0.93 g.; 1H-nmr (CDCl3 ) delta (narrow product peaks only): 3.80 (s, 3H), 6.15 (m, 1H), 6.83 (m, 2H).

Workup

  1. additiondiluted with 10 ml
  2. customthe organic layer separated
  3. washwashed 1×10 ml
  4. dry with materialH2O, dried over Na2SO4

Sources & evidence

ORD record
ord-912f6b843bff4341918d2dfd12f1d583
Source dataset
uspto-grants-1987_06
Patent number
US04675186

Reaction notes

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