Reaktion #671110

Reaktionsgleichung

3,4,5-trimethoxyphenol

triethylamine

4-methoxymetanilyl fluoride

tert-butylammonium iodide

→

desired compound

Ausbeute 35.0%

(3,4,5-trimethoxyphenyl) 3-amino-4-methoxybenzenesulfonate

Ausbeute 35.0%

Lösungsmittel

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Waschenwashed once with 1M Na2CO3
2. 2
   SonstigeThe organic layer was separated
3. 3
   Trocknendried (MgSO4)
4. 4
   Filtrationfiltered
5. 5
   Einengenconcentrated
6. 6
   EinengenChromatography of the concentrate on silica gel with 40% ethyl acetate/hexanes

Vorschrift

A solution of 3,4,5-trimethoxyphenol (505.7 mg, 2.75 mmol) in dichloromethane (28 mL) was treated sequentially with triethylamine (1.2 mL), 4-methoxymetanilyl fluoride (572.5 mg, 2.75 mmol), and tert-butylammonium iodide (106 mg, 0.287 mmol), stirred overnight, and washed once with 1M Na2CO3. The organic layer was separated, dried (MgSO4), filtered, and concentrated. Chromatography of the concentrate on silica gel with 40% ethyl acetate/hexanes provided 356 mg of the desired compound.

Quelle