Bromoacetone → HCID 19010857, compound

HRID 1741822Notes

Reaction equation

HRID 1741822 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][CH2:8][CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12].Br[CH2:17][C:18](=O)[CH3:19]>CC(C)=O>[CH3:19][C:18]1[C:7]([CH2:8][CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:2]2[N:1]([CH:17]=1)[CH:6]=[CH:5][CH:4]=[CH:3]2

Participants

4

Reactant 2

HCID 11715BromoacetoneHCID 11241218Ethyl 5-(pyridin-2-yl)pentanoate

Product 1

HCID 19010857HCID 19010857, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of ethyl 5-(2-pyridyl)pentanoate (1.07 g) in acetone (5 ml) was added bromoacetone (0.51 ml) and the mixture was refluxed for 2 hours. After removal of the solvent, the residue was dissolved in aqueous sodium bicarbonate (1 g sodium bicarbonate/20 ml water) and then refluxed for 30 minutes. The mixture was extracted with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate, evaporated in vacuo, and chromatographed on silica gel (dichloromethane) to give ethyl 4-(2-methylindolizin-1-yl)butyrate (778 mg).

Workup

  1. temperaturethe mixture was refluxed for 2 hours
  2. customAfter removal of the solvent
  3. dissolutionthe residue was dissolved in aqueous sodium bicarbonate (1 g sodium bicarbonate/20 ml water)
  4. temperaturerefluxed for 30 minutes
  5. extractionThe mixture was extracted with ethyl acetate
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried over sodium sulfate
  8. customevaporated in vacuo
  9. customchromatographed on silica gel (dichloromethane)

Sources & evidence

ORD record
ord-cf982f91ad0c4b9cbf588fb0e885bebf
Source dataset
uspto-grants-1994_08
Patent number
US05334716

Reaction notes

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