Reaktion #217614

Reaktionsgleichung

Hydrochloric acid

pentafluorophenol

4-[(phenyhnethyl)oxy]benzenesulfonyl chloride

4-[(Phenylmethyl)oxy]benzenesulfonyl chloride

triethylamine

→

title compound ( D49 )

Pentafluorophenyl 4-[(phenylmethyl)oxy]benzenesulfonate

Lösungsmittel

dichloromethane

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe layers separated
2. 2
   ExtraktionThe aqueous layer was then re-extracted with dichloromethane (100 ml)
3. 3
   Waschenthe combined organic fractions washed with saturated aqueous sodium hydrogen carbonate (200 ml)
4. 4
   SonstigeThe layers were separated
5. 5
   Extraktionthe aqueous re-extracted with dichloromethane (100 ml)
6. 6
   Trocknendried over sodium sulfate
7. 7
   Filtrationfiltered
8. 8
   Sonstigeevaporated
9. 9
   workup.DISSOLUTIONThe resulting solid was then dissolved in dichloromethane (40 ml)
10. 10
    Temperaturwith warming
11. 11
    Temperaturto cool
12. 12
    Sonstigepurified by chromatography on silica gel eluting with 10-15% diethyl ether/hexane

Vorschrift

To a stirred solution of 4-[(phenyhnethyl)oxy]benzenesulfonyl chloride (D48) (13.77 g, 48.70 mmol) in dichloromethane (265 ml) was added triethylamine (9.16 ml, 65.75 mmol) under argon and the mixture cooled to −15° C. A solution of pentafluorophenol (9.86 g, 53.57 mmol) in dichloromethane (20 ml+20 ml wash) was then added quickly and the reaction allowed to wami slowly to room temperature over 1.75 h. Hydrochloric acid (2M, 250 ml) was then added and the mixture stirred for 20-30 min and the layers separated. The aqueous layer was then re-extracted with dichloromethane (100 ml) and the combined organic fractions washed with saturated aqueous sodium hydrogen carbonate (200 ml). The layers were separated and the aqueous re-extracted with dichloromethane (100 ml). All the dichloromethane layers were combined and dried over sodium sulfate, filtered and evaporated. The resulting solid was then dissolved in dichloromethane (40 ml) with warming, and allowed to cool and then purified by chromatography on silica gel eluting with 10-15% diethyl ether/hexane to afford the title compound (D49). 1H-NMR (d6-DMSO) d 7.97-7.94 (2H, m), 7.50-7.31 (7H, m), 5.29 (2H, s).

Quelle