反应详情

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.

1. temperatureto reflux
2. temperatureThe mixture was refluxed for 2 hours
3. customquenched with 1N HCl
4. extractionThe solution was extracted with EtOAc
5. washthe organic layer was washed with 1N NaOH and brine
6. dry with materialdried (MgSO4)
7. concentrationconcentrated
8. customThe residue was chromatographed over silica gel
9. washeluting with 3:2 hexane