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

HRID 5126
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 5126
[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]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

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

Produkt 1

HCID 117896658-Azido-1-octanol

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 1049PyridineLösungsmittel
HCID 6228
Dimethylformamide
Lösungsmittel
HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
10 °C

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-86a11031d1d743c286db830c75a75df3
Quelldatensatz
uspto-grants-1993_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05243035

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