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

HRID 2372431

반응식

HRID 2372431 반응식
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]

참가 물질

7

반응물 5

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
-73 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-3ff5bc31306346dca8e5fcacd697f3f3
출처 데이터셋
uspto-grants-1992_03
특허 번호
US05098928

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