Tetrahydrofuran → HCID 131713235, compound

HRID 1649484Notes

Reaction equation

HRID 1649484 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[N:3][C:2]=1[C:7]1[C:8]([Cl:16])=[CH:9][C:10]([Cl:15])=[C:11]([CH2:13][OH:14])[CH:12]=1.O1CCCC1.[H-].[Na+].[C:24]1([C:30]2[CH:37]=[CH:36][C:33]([CH2:34]Cl)=[CH:32][CH:31]=2)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>O>[C:24]1([C:30]2[CH:31]=[CH:32][C:33]([CH2:34][O:14][CH2:13][C:11]3[CH:12]=[C:7]([C:2]4[N:3]=[CH:4][CH:5]=[CH:6][N:1]=4)[C:8]([Cl:16])=[CH:9][C:10]=3[Cl:15])=[CH:36][CH:37]=2)[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 154634-Phenylbenzyl chlorideHCID 24758Sodium hydrideHCID 70522272HCID 70522272, compound

Product 1

HCID 131713235HCID 131713235, 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 cndensor and an argon inlet was added 3.32 gm of the 5-pyrimidyl-2,4-dichlorophenylcarbinol and 70 ml of anhydrous tetrahydrofuran. The system was cooled to 0° C. and after cooling 0.34 gm sodium hydride was added. The system was stirred for an additional 20 minutes and 3.16 gm of 4-phenylbenzylchloride was then added. The system was allowed to come to room temperature and stirred there for 1 hour. Afterwards, the system was heated at reflux for 48 hours. At this time, water was added to the system and the product extracted with methylene chloride. The methylene chloride extract was washed with water and dried over sodium sulfate. The methylene chloride was removed by stripping to give 3.66 m of the 5-pyrimidyl--2,4-dichlorophenylcarbinol 4-phenylbenzylether --Compound 12 in Table I.

Workup

  1. customTo a 250 ml single neck round bottom flask equipped with a reflux cndensor and an argon inlet
  2. additionwas added
  3. customto come to room temperature
  4. stirringstirred there for 1 hour
  5. temperatureAfterwards, the system was heated
  6. temperatureat reflux for 48 hours
  7. extractionthe product extracted with methylene chloride
  8. extractionThe methylene chloride extract
  9. washwas washed with water
  10. dry with materialdried over sodium sulfate
  11. customThe methylene chloride was removed

Sources & evidence

ORD record
ord-6e5afff14dc749a3bf62c6c7f2a305ec
Source dataset
uspto-grants-1983_11
Patent number
US04417050

Reaction notes

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