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

HRID 5126

반응식

HRID 5126 반응식
[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]

참가 물질

8

반응물 4

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

생성물 1

HCID 117896658-Azido-1-octanol

시약·촉매·용매 3

HCID 1049Pyridine용매HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

반응 조건

온도
10 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-86a11031d1d743c286db830c75a75df3
출처 데이터셋
uspto-grants-1993_09
특허 번호
US05243035

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