Reaktion #975653

Reaktionsgleichung

{4-methoxy-3-[4-nitro-2-(2,2,2-trifluoro-ethylsulfanylmethyl)-phenoxy]-phenyl}-acetic acid ethyl ester

1,1-dimethylhydrazine

DARCO

→

title compound

{3-[4-Amino-2-(2,2,2-trifluoro-ethylsulfanylmethyl)-phenoxy]-4-methoxy-phenyl}-acetic acid ethyl ester

Lösungsmittel

EtOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe mixture was partitioned between EtOAc and H2O
2. 2
   Extraktionextracted three times with EtOAc
3. 3
   WaschenThe combined organic layers were washed with H2O and brine
4. 4
   Trocknendried over MgSO4
5. 5
   Filtrationfiltered
6. 6
   Einengenconcentrated
7. 7
   SonstigeThe residue was purified by silica gel chromatography (EtOAc in hexanes gradient)

Vorschrift

A solution of {4-methoxy-3-[4-nitro-2-(2,2,2-trifluoro-ethylsulfanylmethyl)-phenoxy]-phenyl}-acetic acid ethyl ester (1.46 g, 3.18 mmol), ferric chloride (0.026 g, 0.16 mmol), 1,1-dimethylhydrazine (1.69 mL, 22.27 mmol), and DARCO (0.300 g) in EtOH (30 mL) was stirred overnight at 65° C. The mixture was partitioned between EtOAc and H2O and extracted three times with EtOAc. The combined organic layers were washed with H2O and brine, and then dried over MgSO4, filtered, and concentrated. The residue was purified by silica gel chromatography (EtOAc in hexanes gradient) to give the title compound.

Quelle