Reaktion #53210

Reaktionsgleichung

pyridine

4-(3-hydroxyprop-1-ynyl)-nitrobenzene

p-toluenesulphonic acid chloride

hydrochloric acid

→

4-[3-(p-Tolylsulphonyloxy)-prop-1-ynyl]-nitrobenzene

Lösungsmittel

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe organic phase is separated off
2. 2
   Waschenwashed with water
3. 3
   SonstigeAfter removal of the solvent in vacuo and chromatography of the residue on silica gel (dichloromethane/methanol=1:1) the product
4. 4
   Sonstigeis obtained as an oil

Vorschrift

4.4 ml (54 mmol) of pyridine are added dropwise to a solution of 5.8 g (33 mmol) of 4-(3-hydroxyprop-1-ynyl)-nitrobenzene and 5.2 g (27 mmol) of p-toluenesulphonic acid chloride in 50 ml of dichloromethane at 0° C. After 2 hours at 0° C. about 25 g of ice and 8 ml of conc. hydrochloric acid are added. The organic phase is separated off and washed with water. After removal of the solvent in vacuo and chromatography of the residue on silica gel (dichloromethane/methanol=1:1) the product is obtained as an oil.

Quelle