Reaktion #85726

Reaktionsgleichung

tert-butyl 4-formyl-1H-imidazole-1-carboxylate

(S)-2-methylpropane-2-sulfinamide

→

(S,E)-tert-butyl 4-(((tert-butylsulfinyl)imino)methyl)-1H-imidazole-1-carboxylate

Ausbeute 72.8%

Lösungsmittel

DCE

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction mixture was then cooled to room temperature
2. 2
   Filtrationfiltered through a pad of celite
3. 3
   WaschenThe pad was rinsed with DCM (200 mL)
4. 4
   Einengenthe filtrated was concentrated
5. 5
   EinengenThe filtrate was concentrated

Vorschrift

To CuSO4 (24.28 g, 152 mmol) and tert-butyl 4-formyl-1H-imidazole-1-carboxylate (19.9 g, 101 mmol) in DCE (100 mL) was added (S)-2-methylpropane-2-sulfinamide (13.52 g, 112 mmol). The reaction was heated to 65° C. for 18 hours. The reaction mixture was then cooled to room temperature and filtered through a pad of celite. The pad was rinsed with DCM (200 mL) and the filtrated was concentrated. The residue was then run through a pad of silica gel with heptane/EtOAc (3:1) as eluent. The filtrate was concentrated to give crude (S,E)-tert-butyl 4-(((tert-butylsulfinyl)imino)methyl)-1H-imidazole-1-carboxylate (22 g). LCMS (B) m/z 300.2 (M+H)+

Quelle