반응 #79566

반응 방정식

3-(4-hydroxyphenyl)-1-propanol

NaH

6-bromohexanenitrile

→

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

수율 30.0%

용매

DMF

DMF

반응 조건

후처리

1. 1
   온도the reaction mixture was cooled to 0° C.
2. 2
   workup.STIRRINGstirred for 24 h
3. 3
   기타The reaction mixture was quenched with saturated NaCl solution (200 mL)
4. 4
   추출the product was extracted with EtOAc (300 mL)
5. 5
   세척The organic layer was washed with brine solution
6. 6
   건조dried with Na2SO4
7. 7
   기타evaporated to dryness
8. 8
   기타yielding a pale yellow solid
9. 9
   기타Purification of the crude product by flash silica column chromatography

실험 절차

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).

출처