Reacción #79566

Ecuación de reacción

3-(4-hydroxyphenyl)-1-propanol

NaH

6-bromohexanenitrile

→

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

Rendimiento 30.0%

Disolventes

DMF

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturathe reaction mixture was cooled to 0° C.
2. 2
   workup.STIRRINGstirred for 24 h
3. 3
   OtroThe reaction mixture was quenched with saturated NaCl solution (200 mL)
4. 4
   Extracciónthe product was extracted with EtOAc (300 mL)
5. 5
   LavadoThe organic layer was washed with brine solution
6. 6
   Secadodried with Na2SO4
7. 7
   Otroevaporated to dryness
8. 8
   Otroyielding a pale yellow solid
9. 9
   OtroPurification of the crude product by flash silica column chromatography

Procedimiento

A solution of 3-(4-hydroxyphenyl)-1-propanol (2.0 g, 13.1 mmole) in DMF (5 mL) was added to a solution of DMF (35 mL) containing NaH (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 111 EtOAc/hexane. 1H-NMR (CDCl3, 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).

Fuente