Reacción #590409

Ecuación de reacción

Toluene

toluene

(3,4-bis-benzyloxy-phenyl)-acetonitrile

BrCH2CH2Cl

→

1-(3,4-bis-benzyloxy-phenyl)-cyclopropanecarbonitrile

Rendimiento 66.0%

Disolventes

NaOH

H2O

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturabefore being cooled to room temperature
2. 2
   Otrothe organic layer was separated
3. 3
   Lavadowashed with H2O, brine
4. 4
   Secadodried over anhydrous MgSO4
5. 5
   Concentraciónconcentrated
6. 6
   OtroThe residue was purified by column on silica gel (petroleum ether/ethyl acetate 10:1)

Procedimiento

To a mixture of (n-C4H9)4NBr (0.50 g, 1.5 mmol), toluene (7 mL) and (3,4-bis-benzyloxy-phenyl)-acetonitrile (14 g, 42 mmol) in NaOH (50 g) and H2O (50 mL) was added BrCH2CH2Cl (30 g, 0.21 mol). The reaction mixture was stirred at 50° C. for 5 h before being cooled to room temperature. Toluene (30 mL) was added and the organic layer was separated and washed with H2O, brine, dried over anhydrous MgSO4, and concentrated. The residue was purified by column on silica gel (petroleum ether/ethyl acetate 10:1) to give 1-(3,4-bis-benzyloxy-phenyl)-cyclopropanecarbonitrile (10 g, 66%). 1H NMR (DMSO 300 MHz) δ 7.46-7.30 (m, 10H), 7.03 (d, J=8.4 Hz, 1H), 6.94 (d, J=2.4 Hz, 1H), 6.89 (dd, J=2.4, 8.4 Hz, 1H), 5.12 (d, J=7.5 Hz, 4H), 1.66-1.62 (m, 2H), 1.42-1.37 (m, 2H).

Fuente