Allyl bromide → HCID 131713234, compound

HRID 1649483Notes

Reaction equation

HRID 1649483 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[N:3][C:2]=1[C:7]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:8]=1[CH:9]=[CH:10][CH:11]=[C:12]2[CH2:17][OH:18].O1C[CH2:22][CH2:21][CH2:20]1.[H-].[Na+].C(Br)C=C>O>[CH2:22]([O:18][CH2:17][C:12]1[C:13]2[C:8](=[C:7]([C:2]3[N:3]=[CH:4][CH:5]=[CH:6][N:1]=3)[CH:16]=[CH:15][CH:14]=2)[CH:9]=[CH:10][CH:11]=1)[CH:21]=[CH2:20]

Participants

6

Reactant 4

HCID 7841Allyl bromideHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 70523198HCID 70523198, compound

Product 1

HCID 131713234HCID 131713234, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To a 250 ml single neck round bottom flask equipped with a reflux condensor and an argon inlet is added 2.35 gm of the 5-pyrimidyl-1-naphthylcarbinol and 100 ml of anhydrous tetrahydrofuran. The system is cooled to 0° C. and after cooling 0.26 gm sodium hydride is added. The system is stirred for an additional 20 minutes and 1.1 ml of allyl bromide is added. The system is allowed to come to room temperature over 1/2-hour and is stirred there for an additional 2 hours. Afterwards, the system is heated at reflux for 17 hours. At this time, water is added to the system and the product extracted with methylene chloride. The methylene chloride is then washed with water and dried over sodium sulfate. The methylene chloride is removed by stripping to give the 5-pyrimidyl-1-naphthylcarbinol allylether.

Workup

  1. customTo a 250 ml single neck round bottom flask equipped with a reflux condensor and an argon inlet
  2. additionis added
  3. waitto come to room temperature over 1/2-hour
  4. stirringis stirred there for an additional 2 hours
  5. temperatureAfterwards, the system is heated
  6. temperatureat reflux for 17 hours
  7. extractionthe product extracted with methylene chloride
  8. washThe methylene chloride is then washed with water
  9. dry with materialdried over sodium sulfate
  10. customThe methylene chloride is removed

Sources & evidence

ORD record
ord-63270df18e474d5892bff007a47c3294
Source dataset
uspto-grants-1983_11
Patent number
US04417050

Reaction notes

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