Diethyl Ether → 2-(4-Methylphenyl)indolizine

HRID 248402Notes

Reaction equation

HRID 248402 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH3:7].Br[CH2:9][C:10]([C:12]1[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=1)=O.C(OCC)C>CC(C)=O>[CH3:18][C:15]1[CH:16]=[CH:17][C:12]([C:10]2[CH:7]=[C:2]3[N:1]([CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3]3)=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 79752-MethylpyridineHCID 692722-Bromo-4'-methylacetophenone

Product 1

HCID 3469482-(4-Methylphenyl)indolizineYield 74.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of 2-picoline (5.12 g) in acetone (10 ml) was added 2-bromo-4'-methylacetophenone (10.4 g) in one portion and the mixture was heated at 80° C. for one hour. After addition of diethyl ether, the crystalline product was collected and washed with diethyl ether. After drying in air for several hours, this product was suspended in water (100 ml) and a solution of sodium bicarbonate (21 g) in water (100 ml) was added dropwise to the suspension. The mixture was stirred at ambient temperature for 45 minutes and refluxed for half an hour. The mixture was diluted with methylene chloride and washed with aqueous saturated sodium chloride. The organic layer was separated, dried over potassium carbonate and filtered. The solvent was removed in vacuo and the resulting solid was recrystallized from benzene to give 2-(4-methylphenyl)indolizine (7.51 g).

Workup

  1. customthe crystalline product was collected
  2. washwashed with diethyl ether
  3. customAfter drying in air for several hours
  4. additiona solution of sodium bicarbonate (21 g) in water (100 ml) was added dropwise to the suspension
  5. temperaturerefluxed for half an hour
  6. additionThe mixture was diluted with methylene chloride
  7. washwashed with aqueous saturated sodium chloride
  8. customThe organic layer was separated
  9. dry with materialdried over potassium carbonate
  10. filtrationfiltered
  11. customThe solvent was removed in vacuo
  12. customthe resulting solid was recrystallized from benzene

Sources & evidence

ORD record
ord-5c1e705bb6024f20850cf9d81a91c740
Source dataset
uspto-grants-1993_05
Patent number
US05210092

Reaction notes

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