6-Bromohexanenitrile → 6-(3-[4-(5-Cyanopentyloxy)phenyl]propoxy}hexanenitrile

Temperatur

80 °C

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).

1. additioncontaining Nail (1.31 g, 60% in mineral oil) at 0° C. under nitrogen atmosphere
2. temperaturethe reaction mixture was cooled to 0° C.
3. stirringstirred for 24 h
4. customThe reaction mixture was quenched with saturated NaCl solution (200 mL)
5. extractionthe product was extracted with EtOAc (300 mL)
6. washThe organic layer was washed with brine solution
7. dry with materialdried with Na2SO4
8. customevaporated to dryness
9. customyielding a pale yellow solid
10. customPurification of the crude product by flash silica column chromatography

ORD-Eintrag

ord-7de1b608538947cfb67a7200489897ee

Quelldatensatz

uspto-grants-2008_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07427639B2