Reaktion #51746

Reaktionsgleichung

3-tert-butyl-4-hydroxy-benzoic acid methyl ester

cesium carbonate

N,N-dimethylthiocarbamoyl chloride

→

3-tert-butyl-4-dimethylthiocarbamoyloxy-benzoic acid methyl ester

Lösungsmittel

acetonitrile

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturto reflux
2. 2
   TemperaturThe mixture was refluxed for 2 hours
3. 3
   Sonstigequenched with 1N HCl
4. 4
   ExtraktionThe solution was extracted with EtOAc
5. 5
   Waschenthe organic layer was washed with 1N NaOH and brine
6. 6
   Trocknendried (MgSO4)
7. 7
   Einengenconcentrated
8. 8
   SonstigeThe residue was chromatographed over silica gel
9. 9
   Wascheneluting with 3:2 hexane

Vorschrift

A solution of 3.0 g (14.4 mmol) of 3-tert-butyl-4-hydroxy-benzoic acid methyl ester (Aust. J. Chem., 1978;31:907-916), cesium carbonate (7.04 g, 21.6 mmol), and acetonitrile (50 mL) was heated to reflux and then treated with N,N-dimethylthiocarbamoyl chloride (2.67 g, 21.6 mmol) all at once. The mixture was refluxed for 2 hours, cooled to room temperature, and quenched with 1N HCl. The solution was extracted with EtOAc; the organic layer was washed with 1N NaOH and brine, dried (MgSO4), and concentrated. The residue was chromatographed over silica gel, eluting with 3:2 hexane:EtOAc, to give 3-tert-butyl-4-dimethylthiocarbamoyloxy-benzoic acid methyl ester.

Quelle