Reaktion #62193

Reaktionsgleichung

1-((4-(Benzyloxy)phenyl)isocyanomethylsulfonyl)4-methylbenzene

isonicotinaldehyde

K2CO3

→

white solid

Ausbeute 84.0%

4-(4-(4-(Benzyloxy)phenyl)oxazol-5-yl)pyridine

Ausbeute 84.0%

Lösungsmittel

methanol

DME

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwas heated
2. 2
   Temperaturat reflux for 5 h
3. 3
   SonstigeAfter removal of solvent
4. 4
   Sonstigethe residue was purified by silica gel chromatography (2:1 hexane/EtOAc)

Vorschrift

A mixture of 1-((4-(Benzyloxy)phenyl)isocyanomethylsulfonyl)4-methylbenzene (4.3 g, 11.4 mmol), isonicotinaldehyde (1.34 g, 12.5 mmol) and K2CO3 (3.15 g, 22.8 mmol) in methanol (96 mL ) and DME (30 mL) was heated at reflux for 5 h. After removal of solvent, the residue was purified by silica gel chromatography (2:1 hexane/EtOAc) to provide 2.29 g (84%) of a white solid. 1H NMR (400 MHz, CDCl3) δ: 5.12v (s, 2H), 7.03 (d, 2H), 7.46 (m, 6H), 7.56 (d, 2H), 7.61 (d, 2H), 8.02 (s, 1H), 8.58 (d, 2H). MS m/z: 329 [M+1]+.

Quelle