反応 #7830

反応方程式

[4-(1,3-Benzoxazol-2-yl)-2-methoxyphenyl]acetonitrile

Sodium bis(trimethylsilyl)amide

1,4-dibromobutane

→

1-[4-(1,3-benzoxazol-2-yl)-2-methoxyphenyl]cyclopentanecarbonitrile

溶媒

THF

反応条件

後処理

1. 1
   濃縮After concentrating
2. 2
   その他reaction mixture in vacuo
3. 3
   その他the resulting pink oil was purified by flash chromatography
4. 4
   洗浄a gradient elution of 1:9 EtOAc

実験手順

[4-(1,3-Benzoxazol-2-yl)-2-methoxyphenyl]acetonitrile (130 mg, 0.49 mmol) in THF (5.0 mL) was cooled to −78° C. under argon atmosphere. Sodium bis(trimethylsilyl)amide (1.8 mL, 1.08 mmol) was added slowly and after fifteen minutes, added 1,4-dibromobutane (0.07 mL, 0.59 mmol) to dark brown reaction mixture. Let mixture warm to rt overnight. After concentrating reaction mixture in vacuo, the resulting pink oil was purified by flash chromatography, using a gradient elution of 1:9 EtOAc:hexanes to 1:4 EtOAc:hexanes. This afforded the desired compound, 1-[4-(1,3-benzoxazol-2-yl)-2-methoxyphenyl]cyclopentanecarbonitrile, as a yellow solid. 1H NMR(CDCl3, 300 MHz) δ 7.86–7.26 (m, 7H), 4.07 (s, 3H), 2.59–1.91 (m, 8H). MS (ESI) 319.1 (M+H)+.

出典