تفاعل #7830

معادلة التفاعل

[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

المذيبات

THF

ظروف التفاعل

المعالجة

1. 1
   تركيزAfter concentrating
2. 2
   أخرىreaction mixture in vacuo
3. 3
   أخرىthe resulting pink oil was purified by flash chromatography
4. 4
   غسيلa gradient elution of 1:9 EtOAc

الإجراء التجريبي

[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)+.

المصدر