1,2-Dimethoxyethane → HCID 67183225, compound

HRID 644804Notes

Reaction equation

HRID 644804 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[NH:7][CH:8]=1)([O-:3])=[O:2].[K].Br[CH:16]1[CH2:20][CH2:19][CH2:18][CH2:17]1.COCCOC>CN(C=O)C.[Cl-].[Na+].O>[CH:16]1([N:7]2[CH:8]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=[C:6]2[C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:20][CH2:19][CH2:18][CH2:17]1

Participants

7

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 8728BromocyclopentaneHCID 242169Ethyl 4-Nitropyrrole-2-carboxylateHCID 5462222Potassium

Product 1

HCID 67183225HCID 67183225, compoundYield 32.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
80 °C

Procedure

Ethyl 4-nitro-1H-pyrrole-2-carboxylate (1.006 g, 5.432 mmol; see Example 1, step (i) above) was dissolved in DMF (20 mL, dry) to which was added potassium metal (0.492 g, 12.582 mmol) then it was heated to 80° C. and then it was left at that temperature for 1 h with stirring. The reaction mixture was cooled to 50-60° C. after which bromocyclopentane (1 mL, 1.390 g, 9.326 mmol) was added followed by KI (1.548 g, 9.326 mmol). The reaction mixture was heated again for 5 h with stirring at 80° C., after which time it was left stirring at room temperature under N2, overnight. The reaction mixture was diluted with brine under N2, at room temperature, and then it was extracted with ethyl acetate (3×100 mL). The combined organic extract was dried over MgSO4, filtered and the solvent removed under reduced pressure to give the crude product (containing some DME). The product was purified using column chromatography [silica gel, 1/10 ethyl acetate/n-hexane (RF=0.24)]. Fractions containing the pure material were collected and the solvent removed to give pale yellow oil (440 mg, 32% yield).

Workup

  1. additionwas added
  2. temperatureThe reaction mixture was heated again for 5 h
  3. stirringwith stirring at 80° C.
  4. waitafter which time it was left
  5. stirringstirring at room temperature under N2, overnight
  6. extractionit was extracted with ethyl acetate (3×100 mL)
  7. extractionThe combined organic extract
  8. dry with materialwas dried over MgSO4
  9. filtrationfiltered
  10. customthe solvent removed under reduced pressure
  11. customto give the crude product (
  12. customThe product was purified
  13. additionFractions containing the pure material
  14. customwere collected
  15. customthe solvent removed

Sources & evidence

ORD record
ord-72350d42a98940ff97e87d0b53f9e695
Source dataset
uspto-grants-2010_04
Patent number
US07700765B2

Reaction notes

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