Dimethylformamide → HCID 86736354, compound

HRID 1391027Notes

Reaction equation

HRID 1391027 reaction equation
Br[CH2:2][C:3]([O:5][CH3:6])=[O:4].[CH3:7][CH:8]1[CH:12]=[CH:11][CH:10]([CH3:13])[NH:9]1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[CH3:7][C@H:8]1[CH:12]=[CH:11][C@H:10]([CH3:13])[N:9]1[CH2:2][C:3]([O:5][CH3:6])=[O:4]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 1010662,5-Dimethyl-3-pyrroline

Product 1

HCID 86736354HCID 86736354, compoundYield 41.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Methyl bromoacetate (16.8 g, 0.11 mol) was added, dropwise, to a stirred mixture of 2,5-dimethyl-3-pyrroline (10 g, 0.1 mol), potassium carbonate (13.8 g, 0.1 mol), and dimethylformamide (25 cm3) maintained below 30° C. by ice cooling. After addition was complete the mixture was cooled in ice for a further 1 h, then stirred at room temperature overnight. The reaction mixture was then diluted with water (50 cm3) and the product extracted into ether. The ether extract was dried and evaporated to yield an oil* which was distilled under vacuum to give methyl (trans-2,5-dihydro-2,5-dimethyl-1H-pyrrol-1-yl)acetate (7 g) b.p. 89°-92° C./15 mm.

Workup

  1. temperaturemaintained below 30° C. by ice cooling
  2. additionAfter addition
  3. temperaturewas cooled in ice for a further 1 h
  4. extractionthe product extracted into ether
  5. extractionThe ether extract
  6. customwas dried
  7. customevaporated
  8. customto yield an oil* which
  9. distillationwas distilled under vacuum

Sources & evidence

ORD record
ord-f367dd0e3fdc4d8ea113c5aa9b1e2267
Source dataset
uspto-grants-1979_02
Patent number
US04140793

Reaction notes

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