Sodium Chloride → 1,1-Bis(methylthio)-2-(4-phenoxyphenyl)-1 butene

HRID 2372431

反応式

HRID 2372431 の反応式
C[Si]([CH:5]([S:8][CH3:9])[S:6][CH3:7])(C)C.CCCCCC.C([Li])CCC.[CH:21]1[CH:26]=[CH:25][C:24]([C:27]([CH2:29][CH2:30][O:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=O)=[CH:23][CH:22]=1.[Cl-].[Na+]>O1CCCC1>[CH3:7][S:6][C:5]([S:8][CH3:9])=[C:25]([C:24]1[CH:23]=[CH:22][C:30]([O:31][C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)=[CH:29][CH:27]=1)[CH2:26][CH3:21]

参加物

7

反応物 5

HCID 5234Sodium ChlorideHCID 8058HexaneHCID 38763553-Phenoxy-1-phenylpropan-1-oneHCID 11008541Bis(methylthio)(trimethylsilyl)methaneHCID 178418339Butyllithium

生成物 1

HCID 146741331,1-Bis(methylthio)-2-(4-phenoxyphenyl)-1 butene収率 96.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-73 °C

実験手順

Trimethylsilyl-bis(methylthio)methane, 2.65 g, was dissolved in 15 ml of tetrahydrofuran and 7 ml of 1.6 mole hexane solution of n-butyl lithium was dropwise added to the solution in an argon flow under ice cooling. The mixture was stirred at the same temperature for 30 minutes. After cooling to -73° C., a solution of 2.26 g of 4-phenoxypropiophenone in 5 ml of tetrahydrofuran was dropwise added to the mixture. Then, the temperature was gradually elevated to room temperature followed by stirring for 16 hours. After saturated sodium chloride aqueous solution was added to the mixture, it was extracted with chloroform. After drying the chloroform phase over magnesium sulfate, the solvent was distilled off under reduced pressure and the residue was purified by silica gel column chromatography (chloroform : hexane =1 : 1) to give 3.04 g of the oily product.

後処理

  1. customwas gradually elevated to room temperature
  2. stirringby stirring for 16 hours
  3. extractionwas extracted with chloroform
  4. dry with materialAfter drying the chloroform phase over magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (chloroform : hexane =1 : 1)

出典と根拠

ORDレコード
ord-3ff5bc31306346dca8e5fcacd697f3f3
出典データセット
uspto-grants-1992_03
特許番号
US05098928

関連ノート

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