Reaktion #7830

Reaktionsgleichung

[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

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   EinengenAfter concentrating
2. 2
   Sonstigereaction mixture in vacuo
3. 3
   Sonstigethe resulting pink oil was purified by flash chromatography
4. 4
   Waschena gradient elution of 1:9 EtOAc

Vorschrift

[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)+.

Quelle