Water → HCID 67258011, compound

HRID 1844300Notes

Reaction equation

HRID 1844300 reaction equation
[NH:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([O:8][CH3:9])=[O:7].[H-].[Na+].[F:12][CH2:13][CH2:14]I.O>CN(C=O)C>[F:12][CH2:13][CH2:14][N:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([O:8][CH3:9])=[O:7]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 69804Ethane, 1-fluoro-2-iodo-HCID 136930Methyl pyrrole-2-carboxylate

Product 1

HCID 67258011HCID 67258011, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methyl 1H-pyrrole-2-carboxylate (3.0 g, 23.3 mmol) was solved in DMF (40 ml). Sodium hydride (1.40 g, 34.9 mmol, 60% in oil) was added and the mixture was stirred for 30 minutes at room-temperature. 1-Fluoro-2-iodoethane (4.1 g, 23.2 mmol) was added and the mixture was stirred for 15 h at 50° C. Water was added and the mixture was extracted with diethylether. The mixture was washed with saturated aqueous ammonium chloride. The product was purified chromatographically, using a mixture of petroleum and ethylacetate as eluent. Yield 1.1 g (28%).

Workup

  1. stirringthe mixture was stirred for 15 h at 50° C
  2. extractionthe mixture was extracted with diethylether
  3. washThe mixture was washed with saturated aqueous ammonium chloride
  4. customThe product was purified chromatographically
  5. additiona mixture of petroleum and ethylacetate as eluent

Sources & evidence

ORD record
ord-5ebfebd9533542bcb998650c490ea704
Source dataset
uspto-grants-2015_02
Patent number
US08946412B2

Reaction notes

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