4-Toluenesulfonyl chloride → 1,1,1-Tris(tosylethoxymethyl)ethane

HRID 36829ノート

反応式

HRID 36829 の反応式
O[CH2:2][CH2:3][O:4][CH2:5][C:6]([CH2:13][O:14][CH2:15][CH2:16]O)([CH2:8][O:9][CH2:10][CH2:11]O)[CH3:7].[C:18]1([CH3:28])[CH:23]=[CH:22][C:21]([S:24](Cl)(=[O:26])=[O:25])=[CH:20][CH:19]=1>N1C=CC=CC=1>[S:24]([CH2:16][CH2:15][O:14][CH2:13][C:6]([CH2:5][O:4][CH2:3][CH2:2][S:24]([C:21]1[CH:22]=[CH:23][C:18]([CH3:28])=[CH:19][CH:20]=1)(=[O:26])=[O:25])([CH2:8][O:9][CH2:10][CH2:11][S:24]([C:21]1[CH:22]=[CH:23][C:18]([CH3:28])=[CH:19][CH:20]=1)(=[O:26])=[O:25])[CH3:7])([C:21]1[CH:22]=[CH:23][C:18]([CH3:28])=[CH:19][CH:20]=1)(=[O:26])=[O:25]

参加物

4

反応物 2

HCID 73974-Toluenesulfonyl chlorideHCID 22328182Poly(oxy-1,2-ethanediyl), α-hydro-ω-hydroxy-, ether with 2-(hydroxymethyl)-2-methyl-1,3-propanediol (3:1)

生成物 1

HCID 545380091,1,1-Tris(tosylethoxymethyl)ethane収率 50%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

A solution of 1,1,1-tris(hydroxyethoxymethyl)ethane (6.7 g, 0.026 mol) in 35 mL of anhydrous pyridine was cooled to -10° C. Then solid p-toluenesulfonyl chloride (16.6 g, 0.087 mol) was added in portions over 1.5 hrs. The mixture was kept at -10° C. for 15 hrs. The resulting slurry was partitioned between dichloromethane (100 mL) and water (50 mL) and the layers were separated. The organic layer was washed with water (50 mL), dried over anhydrous sodium sulfate and evaporated to give a crude gum. This material was purified over silica gel using 1% methanol/dichloromethane as eluant to give 1,1,1-tris(tosylethoxymethyl)ethane (8.9 g, 0.013 mol, 47%).

後処理

  1. customThe resulting slurry was partitioned between dichloromethane (100 mL) and water (50 mL)
  2. customthe layers were separated
  3. washThe organic layer was washed with water (50 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. customevaporated
  6. customto give a crude gum
  7. customThis material was purified over silica gel using 1% methanol/dichloromethane as eluant

出典と根拠

ORDレコード
ord-c7b29fdc701a4a23a41d1576ba2c2b8d
出典データセット
uspto-grants-1995_05
特許番号
US05417959

反応ノート

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