Allyl bromide → HCID 54528127, compound

HRID 262730Notes

Reaction equation

HRID 262730 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[CH2:7][C@H:8]3[NH:19][CH2:18][CH2:17][C@@:14]4([C:15]=2[CH:16]=1)[C@H:9]3[CH2:10][CH2:11][O:12][CH2:13]4.[CH2:20](Br)[CH:21]=[CH2:22].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH2:22]([N:19]1[CH2:18][CH2:17][C@@:14]23[C:15]4[CH:16]=[C:3]([O:2][CH3:1])[CH:4]=[CH:5][C:6]=4[CH2:7][C@@H:8]1[C@@H:9]2[CH2:10][CH2:11][O:12][CH2:13]3)[CH:21]=[CH2:20]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 13690878HCID 13690878, compound

Product 1

HCID 54528127HCID 54528127, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 3-methoxy-6-oxamorphinan (VIII) (0.005 m), allyl bromide (0.006 m) and potassium carbonate (2 g) in 20 ml acetonitrile is heated at reflux for 18 hours. The mixture is filtered and the filtrate concentrated. The residue is treated with water and extracted with ethyl acetate. The extracts are dried (Na2SO4) and concentrated to give the title compound.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 18 hours
  3. filtrationThe mixture is filtered
  4. concentrationthe filtrate concentrated
  5. additionThe residue is treated with water
  6. extractionextracted with ethyl acetate
  7. dry with materialThe extracts are dried (Na2SO4)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-1f382d38c7da499b8a85996fb563eaee
Source dataset
uspto-grants-1979_05
Patent number
US04154932

Reaction notes

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