Tetrahydrofuran → HCID 131713233, compound

HRID 1649482Notes

Reaction equation

HRID 1649482 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[N:3][C:2]=1[C:7]1[C:8]([O:15][CH3:16])=[CH:9][CH:10]=[C:11]([CH2:13][OH:14])[CH:12]=1.O1CCCC1.[H-].[Na+].[F:24][C:25]([F:35])([F:34])[C:26]1[CH:27]=[C:28]([CH:31]=[CH:32][CH:33]=1)[CH2:29]Cl>O>[F:24][C:25]([F:34])([F:35])[C:26]1[CH:27]=[C:28]([CH:31]=[CH:32][CH:33]=1)[CH2:29][O:14][CH2:13][C:11]1[CH:12]=[C:7]([C:2]2[N:3]=[CH:4][CH:5]=[CH:6][N:1]=2)[C:8]([O:15][CH3:16])=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 697163-(Trifluoromethyl)benzyl chlorideHCID 70522793HCID 70522793, compound

Product 1

HCID 131713233HCID 131713233, 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 was added 3.24 gm of the 5-pyrimidyl-4-methoxyphenylcarbinol and 70 ml of anhydrous tetrahydrofuran. The system was cooled to 0° C. and after cooling 0.45 gm of sodium hydride was added. The system was stirred for an additional 20 minutes and 2.8 ml of 3-trifluoromethylbenzylchloride added. The system was allowed to come to room temperature and was then heated to reflux for 20 hours at this time, water was added to the system and the product extracted with methylene chloride. The methylene chloride was washed with water and then dried over sodium sulfate. The methylene chloride was removed by stripping to give 4.13 gm of the 5-pyrimidyl-4-methoxyphenylcarbinol 3-trifluoromethylbenzylether as an orange oil and listed as Compound No. 7 in Table I.

Workup

  1. customTo a 250 ml single neck round bottom flask equipped with a reflux condensor and an argon inlet
  2. additionwas added
  3. customto come to room temperature
  4. temperaturewas then heated
  5. additionwas added to the system
  6. extractionthe product extracted with methylene chloride
  7. washThe methylene chloride was washed with water
  8. dry with materialdried over sodium sulfate
  9. customThe methylene chloride was removed

Sources & evidence

ORD record
ord-73a918c6e54d4797b91cf46d328ee56a
Source dataset
uspto-grants-1983_11
Patent number
US04417050

Reaction notes

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