Dimethylformamide → HCID 70605653, compound

HRID 1391029Notes

Reaction equation

HRID 1391029 reaction equation
Br[CH:2]([CH3:8])[C:3]([O:5][CH2:6][CH3:7])=[O:4].[CH3:9][C@H:10]1[CH:14]=[CH:13][C@H:12]([CH3:15])[NH:11]1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[CH3:9][C@H:10]1[CH:14]=[CH:13][C@H:12]([CH3:15])[N:11]1[CH:2]([CH3:8])[C:3]([O:5][CH2:6][CH3:7])=[O:4]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 79040Ethyl 2-bromopropionateHCID 7003741trans-2,5-dimethyl-3-pyrroline

Product 1

HCID 70605653HCID 70605653, compoundYield 24.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Ethyl 2-bromopropionate (9.8 g.) was added, dropwise, to a stirred mixture of trans-2,5-dimethyl-3-pyrroline (5 g.), potassium carbonate (6.9 g.), and dimethylformamide (12.5 cm3) maintained below 30° C. by external cooling. After addition was complete the mixture was stirred at room temperature overnight. The mixture was then diluted with water (25 cm3) and the product extracted into ether. The ether extract was dried and evaporated to give an oil which was distilled under vacuum to give ethyl 2-(trans-2,5-dimethyl-2,5-dihydro-1H-pyrrol-1-yl)propionate (2.5 g.) b.p. 90°-97° C./15 mm.

Workup

  1. temperaturemaintained below 30° C. by external cooling
  2. additionAfter addition
  3. extractionthe product extracted into ether
  4. extractionThe ether extract
  5. customwas dried
  6. customevaporated
  7. customto give an oil which
  8. distillationwas distilled under vacuum

Sources & evidence

ORD record
ord-af39102256364b8684a1f7c768fecbd2
Source dataset
uspto-grants-1979_02
Patent number
US04140793

Reaction notes

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