Dimethyl Sulfoxide → HCID 21476919、化合物

HRID 2293579ノート

反応式

HRID 2293579 の反応式
[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([CH2:10][C:11]([NH:13][S:14]([C:17]3[CH:22]=[CH:21][C:20]([CH:23]([CH3:25])[CH3:24])=[CH:19][CH:18]=3)(=[O:16])=[O:15])=[O:12])=[CH:4][C:3]=2[O:2]1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].CS(C)=O.Br[CH2:41][C:42]1[CH:47]=[CH:46][C:45]([C:48]([F:51])([F:50])[F:49])=[CH:44][CH:43]=1>C1COCC1>[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([CH:10]([CH2:41][C:42]3[CH:43]=[CH:44][C:45]([C:48]([F:49])([F:50])[F:51])=[CH:46][CH:47]=3)[C:11]([NH:13][S:14]([C:17]3[CH:22]=[CH:21][C:20]([CH:23]([CH3:25])[CH3:24])=[CH:19][CH:18]=3)(=[O:16])=[O:15])=[O:12])=[CH:4][C:3]=2[O:2]1

参加物

6

反応物 4

HCID 679Dimethyl SulfoxideHCID 1230621-(Bromomethyl)-4-(trifluoromethyl)benzeneHCID 2733832Lithium HexamethyldisilazideHCID 21476920HCID 21476920、化合物

生成物 1

HCID 21476919HCID 21476919、化合物収率 28.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-78 °C

実験手順

To a suspension of 0.992 g (0.27 mmol) of the product of Example 1 in 0.5 mL of anhydrous THF was added 825 μL (0.82 mmol) of a 1.0M solution of lithium bis(trimethylsilyl)amide in THF at -78° C. under a nitrogen atmosphere. After stirring at -78° C. for 10 minutes, the starting material had not fully dissolved. The reaction mixture was then warmed to 0° C. (ice-water bath) and 300 μL of DMSO was added which resulted in a clear yellow solution, then 0.131 g (0.55 mmol) of α'-bromo-α,α,α-trifluoro-p-xylene was added as a solid. Stirring was maintained for 1 hour, then the reaction mixture was partitioned between EtOAc and water and extracted. The organic layer was washed with saturated brine, dried (MgSO4), filtered and evaporated. The residue was purified on a silica gel flash chromatography column eluted with 2.5% MeOH--CHCl3. Evaporation of the product fractions and drying in vacuo afforded 0.040 g (28%) of the title compound.

後処理

  1. dissolutionthe starting material had not fully dissolved
  2. additionwas added which
  3. customresulted in a clear yellow solution
  4. stirringStirring
  5. temperaturewas maintained for 1 hour
  6. customthe reaction mixture was partitioned between EtOAc and water
  7. extractionextracted
  8. washThe organic layer was washed with saturated brine
  9. dry with materialdried (MgSO4)
  10. filtrationfiltered
  11. customevaporated
  12. customThe residue was purified on a silica gel flash chromatography column
  13. washeluted with 2.5% MeOH
  14. customEvaporation of the product fractions
  15. customdrying in vacuo

出典と根拠

ORDレコード
ord-17f07d8ce02448cb879640cfe7d7c92a
出典データセット
uspto-grants-1997_11
特許番号
US05686478

反応ノート

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