Allyl bromide → HCID 70585053, compound

HRID 903623Notes

Reaction equation

HRID 903623 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@@:9]3([OH:20])[CH2:10][CH2:11][O:12][CH2:13]4.[CH2:21](Br)[CH:22]=[CH2:23].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH2:23]([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@:9]2([OH:20])[CH2:10][CH2:11][O:12][CH2:13]3)[CH:22]=[CH2:21]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 57293339HCID 57293339, compound

Product 1

HCID 70585053HCID 70585053, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 3-methoxy-14β-hydroxy-6-oxamorphinan (X) (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-79fcdc5b632a445f831f8d9d9abe0ef4
Source dataset
uspto-grants-1980_10
Patent number
US04228285

Reaction notes

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