Allyl bromide → HCID 20360231, compound

HRID 436256Notes

Reaction equation

HRID 436256 reaction equation
[CH:1]12[CH2:15][CH:6]([C:7](=[O:14])[C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=31)[CH2:5][NH:4][CH2:3][CH2:2]2.C(=O)([O-])[O-].[Na+].[Na+].[CH2:22](Br)[CH:23]=[CH2:24]>C(O)C>[CH2:24]([N:4]1[CH2:3][CH2:2][CH:1]2[CH2:15][CH:6]([CH:7]([OH:14])[C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=32)[CH2:5]1)[CH:23]=[CH2:22]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 10340Sodium CarbonateHCID 20360238HCID 20360238, compound

Product 1

HCID 20360231HCID 20360231, compoundYield 74.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

20 ml of ethanol was added to 1 g of 2,3,4,5-tetrahydro-1,6-methano-1H-4-benzazonin-7(6H)-one and 0.63 g of sodium carbonate, and the mixture was heated and refluxed. Then, 0.72 g of allyl bromide was gradually added to the mixture, and the reaction mixture liquid was heated and refluxed for 5 hours. The mixture was cooled and filtered, and methanol and excessive allyl bromide were distilled from the filtrate. The residue was dissolved in 20 ml of methanol and cooled with ice water, and 0.15 g of sodium boron hydride was gradually added to the solution under agitation. Then, the mixture was agitated at room temperature for 2 hours. Methanol was distilled from the reaction mixture, and 15 ml of water was added to the residue and the mixture was shaken sufficiently. Then, the mixture was extracted with ether and the extract was subjected to distillation to remove ether therefrom. The residue was recrystallized from cyclohexane to obtain 0.9 g of 4-allyl-2,3,4,5,6,7-hexahydro-1,6-methano-1H-4 -benzazonin-7-ol in the form of a white crystal melting at 98° to 100° C.

Workup

  1. temperaturethe mixture was heated
  2. temperaturerefluxed
  3. temperaturethe reaction mixture liquid was heated
  4. temperaturerefluxed for 5 hours
  5. temperatureThe mixture was cooled
  6. filtrationfiltered
  7. distillationmethanol and excessive allyl bromide were distilled from the filtrate
  8. dissolutionThe residue was dissolved in 20 ml of methanol
  9. temperaturecooled with ice water, and 0.15 g of sodium boron hydride
  10. additionwas gradually added to the solution under agitation
  11. distillationMethanol was distilled from the reaction mixture, and 15 ml of water
  12. additionwas added to the residue
  13. stirringthe mixture was shaken sufficiently
  14. extractionThen, the mixture was extracted with ether
  15. distillationthe extract was subjected to distillation
  16. customto remove ether
  17. customThe residue was recrystallized from cyclohexane

Sources & evidence

ORD record
ord-130a827562424bdc9adacbd8af091fbb
Source dataset
uspto-grants-1977_02
Patent number
US04008219

Reaction notes

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