反応 #61066

反応方程式

3-(4hydroxyphenyl)-1-propanol

6-bromohexanenitrile

→

6-{3-[4-(5-cyanopentyloxy)phenyl]propoxy}hexanenitrile

収率 30.0%

溶媒

DMF

DMF

反応条件

後処理

1. 1
   workup.ADDITIONcontaining Nail (1.31 g, 60% in mineral oil) at 0° C. under nitrogen atmosphere
2. 2
   温度the reaction mixture was cooled to 0° C.
3. 3
   workup.STIRRINGstirred for 24 h
4. 4
   その他The reaction mixture was quenched with saturated NaCl solution (200 mL)
5. 5
   抽出the product was extracted with EtOAc (300 mL)
6. 6
   洗浄The organic layer was washed with brine solution
7. 7
   乾燥dried with Na2SO4
8. 8
   その他evaporated to dryness
9. 9
   その他yielding a pale yellow solid
10. 10
    その他Purification of the crude product by flash silica column chromatography

実験手順

A solution of 3-(4hydroxyphenyl)-1-propanol (2.0 g, 13.1 mmole) in DMF (5 mL) was added to a solution of DMF (35 mL) containing Nail (1.31 g, 60% in mineral oil) at 0° C. under nitrogen atmosphere. The reaction mixture was slowly warmed to 80° C. After stirring for 1 h at 80° C., the reaction mixture was cooled to 0° C., and 6-bromohexanenitrile (5.78 g,.32.83 mmole) was added. The final mixture was re-heated to 80° C., and stirred for 24 h. The reaction mixture was quenched with saturated NaCl solution (200 mL), and the product was extracted with EtOAc (300 mL). The organic layer was washed with brine solution, dried with Na2SO4, and evaporated to dryness, yielding a pale yellow solid. Purification of the crude product by flash silica column chromatography: 4/1 to 1/1 hexane/EtOAc provided 6-{3-[4-(5-cyanopentyloxy)phenyl]propoxy}hexanenitrile in 30% yield (1.33 g). Rf=0.63 in 1/1 EtOAc/hexane. 1H-NMR (CDC3, 299.96 MHz): δ (ppm) 7.09-7.07 (d, 2H), 6.81-6.78 (d, 2H), 3.96-3.92 (t, 2H), 3.42-3.37 (m, 4H), 2.64-2.58 (t, 2H), 2.39-2.32 (m, 4H), 1.87-1.52 (m, 14H).

出典