Toluene → 1-(3,4-Bis-benzyloxy-phenyl)-cyclopropanecarbonitrile

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Reaktionsgleichung

[C:1]1(C)C=CC=C[CH:2]=1.[CH2:8]([O:15][C:16]1[CH:17]=[C:18]([CH2:30][C:31]#[N:32])[CH:19]=[CH:20][C:21]=1[O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.BrCCCl>[N+](CCCC)(CCCC)(CCCC)CCCC.[Br-].[OH-].[Na+].O>[CH2:8]([O:15][C:16]1[CH:17]=[C:18]([C:30]2([C:31]#[N:32])[CH2:2][CH2:1]2)[CH:19]=[CH:20][C:21]=1[O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Komponenten

Reaktionsbedingungen

Temperatur: 50 °C

Versuchsvorschrift

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).

Aufarbeitung

temperaturebefore being cooled to room temperature
customthe organic layer was separated
washwashed with H2O, brine
dry with materialdried over anhydrous MgSO4
concentrationconcentrated
customThe residue was purified by column on silica gel (petroleum ether/ethyl acetate 10:1)

Quellen und Nachweise

ORD-Eintrag: ord-74f87dbfe3ac4840b7af41a9009df302
Quelldatensatz: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08623905B2

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