4-Toluenesulfonyl chloride → 8-Azido-1-octanol

HRID 5126

反応式

HRID 5126 の反応式
[CH2:1](O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][OH:9].C1(C)C=CC(S(Cl)(=O)=O)=CC=1.[N-:22]=[N+:23]=[N-:24].[Na+].C(OCC)(=O)C>N1C=CC=CC=1.C(Cl)Cl.CN(C)C=O>[N:22]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][OH:9])=[N+:23]=[N-:24]

参加物

8

反応物 4

HCID 73974-Toluenesulfonyl chlorideHCID 8857Ethyl AcetateHCID 33557Sodium AzideHCID 694201,8-Octanediol

生成物 1

HCID 117896658-Azido-1-octanol

試薬・触媒・溶媒 3

HCID 1049Pyridine溶媒HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
10 °C

実験手順

14.65 g of 1,8-octanediol was dissolved in 80 g of pyridine, and cooled to 10° C. A solution of 19 g p-toluenesulfonyl chloride in 70 ml anhydrous methylene chloride was added dropwise thereto, and the mixture was heated gradually overnight for reaction. After water washing, the solvent was removed by distillation, to produce an oily residue. The residue was dissolved in dimethylformamide to a 200 ml solution, to which was added 20 g of sodium azide, and the resultant mixture was maintained at 80° C. for 2 hours for reaction. The mixture was, after added with ethyl acetate, was washed with water 4 times and the solvent was removed by distillation. The object compound was isolated by silica-gel column-chromatography (CHCl3 -AcOEt 5:1-1:1) The yield was 6.07 g.

後処理

  1. temperaturethe mixture was heated gradually overnight for reaction
  2. customAfter water washing, the solvent was removed by distillation
  3. customto produce an oily residue
  4. washwas washed with water 4 times
  5. customthe solvent was removed by distillation
  6. customThe object compound was isolated by silica-gel column-chromatography (CHCl3 -AcOEt 5:1-1:1) The yield was 6.07 g

出典と根拠

ORDレコード
ord-86a11031d1d743c286db830c75a75df3
出典データセット
uspto-grants-1993_09
特許番号
US05243035

関連ノート

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