Toluene → 5-Decyl-2-(4-(5-ethoxy-2,2,3,3,4,4-hexafluoropentoxy)phenyl)pyrimidine

HRID 1608909Notes

Reaction equation

HRID 1608909 reaction equation
[H-].[Na+].C1(C)C=CC=CC=1.[CH2:10]([C:20]1[CH:21]=[N:22][C:23]([C:26]2[CH:31]=[CH:30][C:29]([OH:32])=[CH:28][CH:27]=2)=[N:24][CH:25]=1)[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19].FC(F)(F)S(O[CH2:39][C:40]([F:52])([F:51])[C:41]([F:50])([F:49])[C:42]([F:48])([F:47])[CH2:43][O:44][CH2:45][CH3:46])(=O)=O>O.CN(C)C=O>[CH2:10]([C:20]1[CH:21]=[N:22][C:23]([C:26]2[CH:27]=[CH:28][C:29]([O:32][CH2:39][C:40]([F:51])([F:52])[C:41]([F:49])([F:50])[C:42]([F:48])([F:47])[CH2:43][O:44][CH2:45][CH3:46])=[CH:30][CH:31]=2)=[N:24][CH:25]=1)[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]

Participants

7

Reactant 4

HCID 1140TolueneHCID 24758Sodium hydrideHCID 218325442,2,3,3,4,4-Hexafluoro-5-ethoxypentyl trifluoromethanesulfonateHCID 135585902Phenol, 4-(5-decyl-2-pyrimidinyl)-

Product 1

HCID 200827435-Decyl-2-(4-(5-ethoxy-2,2,3,3,4,4-hexafluoropentoxy)phenyl)pyrimidineYield 36.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Procedure

0.4 g of sodium hydride (97% pure), 15 ml of toluene and 15 ml of anhydrous N,N-dimethylformamide were placed in a 100 flask fitted with a magnetic stir bar and water-cooled condensor with a dry nitrogen inlet. Then 3.3 g (0.0106 moles) of 5-decyl-2-(4-hydroxyphenyl)pyrimidine was slowly added. After stirring for 30 minutes at room temperature, 3.9 g (0.0106 moles) of 5-ethoxy-2,2,3,3,4,4-hexafluoropentyl trifluoromethanesulfonate (made essentially as in Example 3) was added and the contents stirred overnight at room temperature. The contents then were poured into a separatory funnel containing 30 ml of water. The funnel was shaken and the two layers formed were allowed to separate. The aqueous layer was extracted twice with two 15 ml aliquots of toluene. The organic layers were combined, then washed four times with 20 ml aliquots of deionized water, dried with anhydrous sodium sulphate, and stripped of solvent using a rotary evaporator. The resulting oil was chromatographed on silica gel (chloroform) to obtain 2.07 g of 5-decyl-2-(4-(5-ethoxy-2,2,3,3,4,4-hexafluoropentoxy)phenyl)pyrimidine.

Workup

  1. customfitted with a magnetic stir bar
  2. additionwas added
  3. stirringthe contents stirred overnight at room temperature
  4. additionThe contents then were poured into a separatory funnel
  5. stirringThe funnel was shaken
  6. customthe two layers formed
  7. customto separate
  8. extractionThe aqueous layer was extracted twice with two 15 ml aliquots of toluene
  9. washwashed four times with 20 ml aliquots of deionized water
  10. dry with materialdried with anhydrous sodium sulphate
  11. customa rotary evaporator
  12. customThe resulting oil was chromatographed on silica gel (chloroform)

Sources & evidence

ORD record
ord-bc6a1328beae467ea1202bddfed92009
Source dataset
uspto-grants-1995_03
Patent number
US05399291

Reaction notes

Loading…