Sodium hydride → 5-Butyl-2-(4-(2,2,3,3,4,4-hexafluoro-5-methoxypentoxy)phenyl)pyrimidine

HRID 1608910ノート

反応式

HRID 1608910 の反応式
[H-].[Na+].C([C:7]1[CH:12]=[CH:11][N:10]=[C:9]([C:13]2[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=2)[N:8]=1)CCC.[H][H].FC(F)(F)S(O[CH2:28][C:29]([F:40])([F:39])[C:30]([F:38])([F:37])[C:31]([F:36])([F:35])[CH2:32][O:33][CH3:34])(=O)=O>O.CN(C)C=O.C1(C)C=CC=CC=1>[CH2:9]([C:12]1[CH:11]=[N:10][C:9]([C:13]2[CH:14]=[CH:15][C:16]([O:19][CH2:28][C:29]([F:39])([F:40])[C:30]([F:37])([F:38])[C:31]([F:35])([F:36])[CH2:32][O:33][CH3:34])=[CH:17][CH:18]=2)=[N:8][CH:7]=1)[CH2:13][CH2:14][CH3:15]

参加物

8

反応物 4

HCID 24758Sodium hydrideHCID 157894692,2,3,3,4,4-Hexafluoro-5-methoxypentyl trifluoromethanesulfonateHCID 1356893914-Butyl-2-(4-hydroxyphenyl)pyrimidineHCID 178418361HCID 178418361、化合物

生成物 1

HCID 200827695-Butyl-2-(4-(2,2,3,3,4,4-hexafluoro-5-methoxypentoxy)phenyl)pyrimidine

試薬・触媒・溶媒 3

HCID 962Water溶媒2 回HCID 1140Toluene溶媒HCID 6228Dimethylformamide溶媒

実験手順

Dry sodium hydride (0.5 g, 0.0206 moles) was weighed into a 100 ml flask in a glove bag under dry nitrogen. The flask was then fitted with a magnetic stir bar and a water-cooled condenser with a nitrogen inlet. 20 ml of toluene and 20 ml of anhydrous N,N-dimethylformamide were added, mixing was started, and then 4 g of 4-butyl-2-(4-hydroxyphenyl)pyrimidine (0.0130 moles) was added slowly to control the rate of hydrogen evolution. After stirring at room temperature for 20 minutes, 4.9 g (0.0137 moles) of 2,2,3,3,4,4-hexafluoro-5-methoxypentyl trifluoromethanesulfonate (prepared essentially as in Example 1) was added, and the contents were heated to reflux for 1 hour. After cooling to room temperature, the contents of the flask were poured into a separatory funnel containing 50 ml of water. The funnel was shaken and the two layers formed were allowed to separate. The aqueous layer was extracted twice with 20 ml aliquots of toluene. The organic layers were combined, then were washed three times with 30 ml aliquots of deionized water, dried with anhydrous sodium sulfate, and stripped of solvent using a rotary evaporator. The resulting oil was chromatographed on silica gel, eluting with chloroform, to yield a pale yellow liquid, 5-butyl-2-(4-(2,2,3,3,4,4-hexafluoro-5-methoxypentoxy)phenyl)pyrimidine.

後処理

  1. customThe flask was then fitted with a magnetic stir bar
  2. additionmixing
  3. additionwas added
  4. temperaturethe contents were heated
  5. temperatureto reflux for 1 hour
  6. temperatureAfter cooling to room temperature
  7. additionthe contents of the flask were poured into a separatory funnel
  8. stirringThe funnel was shaken
  9. customthe two layers formed
  10. customto separate
  11. extractionThe aqueous layer was extracted twice with 20 ml aliquots of toluene
  12. washwere washed three times with 30 ml aliquots of deionized water
  13. dry with materialdried with anhydrous sodium sulfate
  14. customa rotary evaporator
  15. customThe resulting oil was chromatographed on silica gel
  16. washeluting with chloroform

出典と根拠

ORDレコード
ord-08119d0d3cc447f0893a44bc7f5fe2e0
出典データセット
uspto-grants-1995_03
特許番号
US05399291

反応ノート

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