Reaktion #62071

Reaktionsgleichung

[6-(6-morpholin-4-yl-4-oxo-4H-pyran-2-yl)-thianthren-2-yl]-carbamic acid tert-butyl ester

trifluoroacetic acid

→

2-(7-Amino-thianthren-1-yl)-6-morpholin-4-yl-pyran-4-one

Lösungsmittel

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.WAITleft
2. 2
   SonstigeThe solvent was dried in vacuo
3. 3
   workup.ADDITIONSaturated sodium bicarbonate solution (400 ml) was added to the residue, which
4. 4
   workup.WAITwas left
5. 5
   workup.STIRRINGto stir for 20 minutes
6. 6
   FiltrationThe brown precipitate was filtered
7. 7
   Waschenwashing with water
8. 8
   workup.WAITleft
9. 9
   Sonstigeto dry in a vacuum desiccator overnight
10. 10
    SonstigeThe solid was then purified by column chromatography (silica, MeOH/Dichloromethane, 3:97, Rf=0.28)

Vorschrift

To a solution of [6-(6-morpholin-4-yl-4-oxo-4H-pyran-2-yl)-thianthren-2-yl]-carbamic acid tert-butyl ester (11.95 g, 23.4 mmol) in dichloromethane (150 ml) was added trifluoroacetic acid (30 ml) and left under stirring at room temperature overnight. The solvent was dried in vacuo revealing a viscous dark brown liquid. Saturated sodium bicarbonate solution (400 ml) was added to the residue, which was left to stir for 20 minutes. The brown precipitate was filtered, washing with water and left to dry in a vacuum desiccator overnight. The solid was then purified by column chromatography (silica, MeOH/Dichloromethane, 3:97, Rf=0.28). 1HNMR (300 MHz, CDCl3): δH=3.24 (2H, bs); 3.46 (4H, bs); 3.81 (4H, bs); 6.33 (1H, s); 6.58 (1H, m); 6.86 (1H, d); 7.21 (1H, d); 7.30 (1H, t); 7.38 (1H, d); 7.63 (1H, d); m/z (LC-MS, ESP), RT=3.8 min, (M++1)=411

Quelle