반응 #7811

반응 방정식

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

sodium cyanide

EtOAc

→

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

용매

DMF H2O

반응 조건

후처리

1. 1
   세척The EtOAc solution was washed with H2O (2×20 mL), brine (2×20 mL)
2. 2
   건조dried (MgSO4)
3. 3
   여과filtered
4. 4
   농축concentrated in vacuo
5. 5
   세척The residue was eluted with flash column (silica gel, hexanes:EtOAc 4:1)

실험 절차

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)+.

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