反応 #7815

反応方程式

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

NaHMDS

1,4-dibromobutane

→

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

溶媒

THF

反応条件

後処理

1. 1
   その他The cooling bath was removed
2. 2
   その他The reaction was quenched by the addition of silica gel (600 mg)
3. 3
   濃縮concentrated to dryness
4. 4
   その他The residue was purified by flash chromatography on silica gel (EtOAc:hexanes 1:5)

実験手順

A solution of [4-(1,3-benzoxazol-2-yl)-2-chlorophenyl]acetonitrile (270 mg, 1.0 mmol) and THF (20 mL) was cooled to −78° C. A solution of NaHMDS (3.7 mL, 2.2 mmol, 0.6M solution in PhMe) was added dropwise via syringe to the reaction. After 15 min at −78° C., 1,4-dibromobutane (143 μL, 1.2 mmol) was added dropwise via syringe. The cooling bath was removed, and the reaction was allowed to warm to rt. The reaction was quenched by the addition of silica gel (600 mg) and concentrated to dryness. The residue was purified by flash chromatography on silica gel (EtOAc:hexanes 1:5) to afford the desired 1-[4-(1,3-benzoxazol-2-yl)-2-chlorophenyl]cyclopentanecarbonitrile as a colorless solid: 1H NMR (CDCl3, 300 MHz) δ 8.34 (s, 1H), 8.12 (dd, 1H), 7.77–7.80 (m, 1H), 7.56–7.62 (m, 2H), 7.35–7.42 (m, 2H), 2.71–2.78 (m, 2H), 2.14–2.26 (m, 2H), 1.89–2.01 (m, 4H). MS (ESI) 323 (M+H)+.

出典