반응 #590409

반응 방정식

Toluene

toluene

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

BrCH2CH2Cl

→

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

수율 66.0%

용매

NaOH

H2O

반응 조건

후처리

1. 1
   온도before being cooled to room temperature
2. 2
   기타the organic layer was separated
3. 3
   세척washed with H2O, brine
4. 4
   건조dried over anhydrous MgSO4
5. 5
   농축concentrated
6. 6
   기타The residue was purified by column on silica gel (petroleum ether/ethyl acetate 10:1)

실험 절차

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).

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