反応 #51746

反応方程式

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

cesium carbonate

N,N-dimethylthiocarbamoyl chloride

→

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

溶媒

acetonitrile

反応条件

後処理

1. 1
   温度to reflux
2. 2
   温度The mixture was refluxed for 2 hours
3. 3
   その他quenched with 1N HCl
4. 4
   抽出The solution was extracted with EtOAc
5. 5
   洗浄the organic layer was washed with 1N NaOH and brine
6. 6
   乾燥dried (MgSO4)
7. 7
   濃縮concentrated
8. 8
   その他The residue was chromatographed over silica gel
9. 9
   洗浄eluting with 3:2 hexane

実験手順

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.

出典