Réaction #7811

Équation de réaction

2-[4-(Bromomethyl)-3-(methoxymethoxy)phenyl]-1,3-benzoxazole

sodium cyanide

EtOAc

→

[4-(1,3-benzoxazol-2-yl)-2-(methoxymethoxy)phenyl]acetonitrile

Solvants

DMF H2O

Conditions de réaction

Traitement

1. 1
   LavageThe EtOAc solution was washed with H2O (2×20 mL), brine (2×20 mL)
2. 2
   Séchagedried (MgSO4)
3. 3
   Filtrationfiltered
4. 4
   Concentrationconcentrated in vacuo
5. 5
   LavageThe residue was eluted with flash column (silica gel, hexanes:EtOAc 4:1)

Mode opératoire

2-[4-(Bromomethyl)-3-(methoxymethoxy)phenyl]-1,3-benzoxazole (250 mg, 0.72 mmol) was treated with sodium cyanide (150 mg, 2.2 mmol) in DMF/H2O (15 mL/1.5 mL) at 90° C. for 3 h and EtOAc (150 mL) was added. The EtOAc solution was washed with H2O (2×20 mL), brine (2×20 mL), dried (MgSO4), filtered, and concentrated in vacuo. The residue was eluted with flash column (silica gel, hexanes:EtOAc 4:1) to afford the desired [4-(1,3-benzoxazol-2-yl)-2-(methoxymethoxy)phenyl]acetonitrile as a yellow solid. 1H NMR (CD3OD, 300 MHz), δ 8.02 (d, 2H), 7.95 (m, 1H), 7.80 (m, 1H), 7.63 (m, 1H), 7.57 (d, 2H), 7.40 (m, 2H). MS (ESI) 295 (M+H)+.

Source