Iodoethane → HCID 12897079, compound

HRID 1980935Notes

Reaction equation

HRID 1980935 reaction equation
[C:1]([C:9]1[NH:13][CH:12]=[C:11]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:10]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O1CC[CH2:21][CH2:20]1.[H-].[Na+].C(I)C>O>[CH2:20]([N:13]1[C:9]([C:1](=[O:8])[C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:10][C:11]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:12]1)[CH3:21]

Participants

6

Reactant 4

HCID 6340Iodoethane4×HCID 8028TetrahydrofuranHCID 24758Sodium hydride4×HCID 20401134HCID 20401134, compound

Product 1

HCID 12897079HCID 12897079, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Ethyl 5-benzoylpyrrole-3-carboxylate (0.973 g., 4 mmoles) was dissolved in 40 ml. of dry tetrahydrofuran. To the stirred solution, under nitrogen, there was added sodium hydride dispersion in oil (57%, 0.173 g., 4 mmoles), and the mixture was stirred for 0.5 hour. Ethyl iodide (1.25 g., 8 mmoles) was added and stirring continued for 6 hours. Additional sodium hydride (0.17 g.) and ethyl iodide (1.25 g.) was added and reflux continued for an additional 104 hours. Like quantities of sodium hydride and ethyl iodide were added after 16 hours reflux and a like quantity of ethyl iodide after 24 hours reflux. The reaction was cooled and excess sodium hydride decomposed by cautious addition of 40 ml. of water. The product was extracted into 40 ml. of ether, the ether back-washed with 10 ml. of water, and evaporated to dryness to yield ethyl 1-ethyl-5-benzoylpyrrole-3-carboxylate (1 g.), used directly in the next step.

Workup

  1. stirringstirring
  2. waitcontinued for 6 hours
  3. temperaturereflux
  4. waitcontinued for an additional 104 hours
  5. temperaturereflux
  6. temperatureThe reaction was cooled
  7. extractionThe product was extracted into 40 ml
  8. washof ether, the ether back-washed with 10 ml
  9. customof water, and evaporated to dryness

Sources & evidence

ORD record
ord-543a7d1747cf40b095fcf3684d1c0b58
Source dataset
uspto-grants-1985_04
Patent number
US04511575

Reaction notes

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