Reaktion #9045

Reaktionsgleichung

alcohol

N, N′-bis-(tert-butoxycarbonyl)-N″-(4-hydroxymethyl-phenyl)-guanidine

→

N, N′-bis-(tert-butoxycarbonyl)-N″-(4-formyl-phenyl)-guanidine

Ausbeute 93.0%

Lösungsmittel

CH2Cl2

Reaktionsbedingungen

Aufarbeitung

1. 1
   FiltrationThe mixture was filtered through celite®
2. 2
   Waschenthe cake was washed with CH2Cl2
3. 3
   SonstigeThe solvent was removed from the filtrate under reduced pressure

Vorschrift

The alcohol (0.282 g, 0.771 mmol) from above was dissolved in CH2Cl2 (7 mL), treated with activated MnO2 (0.696 g, 8.01 mmol) and stirred at room temperature overnight. The mixture was filtered through celite® and the cake was washed with CH2Cl2. The solvent was removed from the filtrate under reduced pressure and provided N, N′-bis-(tert-butoxycarbonyl)-N″-(4-formyl-phenyl)-guanidine (0.260 g, 93%) as a white solid. 1H NMR (CDCl3) δ 1.53 (s, 9H), 1.55 (s, 9H), 7.85 (s, 4H), 9.93 (s, 1H), 10.34 (br s, 1H).

Quelle