Reaktion #983046

Reaktionsgleichung

3-(4hydroxyphenyl)-1-propanol

NaH

6-bromohexanenitrile

→

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

Ausbeute 30.0%

Lösungsmittel

DMF

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe reaction mixture was cooled to 0° C.
2. 2
   workup.STIRRINGstirred for 24 h
3. 3
   SonstigeThe reaction mixture was quenched with saturated NaCl solution (200 mL)
4. 4
   Extraktionthe product was extracted with EtOAc (300 mL)
5. 5
   WaschenThe organic layer was washed with brine solution
6. 6
   Trocknendried with Na2SO4
7. 7
   Sonstigeevaporated to dryness
8. 8
   Sonstigeyielding a pale yellow solid
9. 9
   SonstigePurification of the crude product by flash silica column chromatography

Vorschrift

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 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 1/1 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, 14 H).

Quelle