Diethyl (cyanomethyl)phosphonate → 3-(3,4-Dimethoxyphenyl)-3-(2-furyl)acrylonitrile
Reaktionsgleichung
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]([C:17]2C=C[C:20]([O:23]C)=[C:19](OC)[CH:18]=2)=[CH:12][C:13](OC)=O)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].COC1C=C(C=CC=1OC)C(C1OC=CC=1)=O.C(OP(CC#[N:54])(=O)OCC)C.C[Si](C)(C)[N-][Si](C)(C)C.[Li+]>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]([C:17]2[O:23][CH:20]=[CH:19][CH:18]=2)=[CH:12][C:13]#[N:54])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]Komponenten
Versuchsvorschrift
3-(3,4-Dimethoxyphenyl)-3-(2-furyl)acrylonitrile was prepared analogously to methyl 3,3-bis-(3′,4′-dimethoxyphenyl)acrylate using 2-(3,4-dimethoxybenzoyl)furane (0.87 g, 4 mmol), diethylcyanomethylphosphonate (0.73 mL, 4.4 mmol) and lithium hexamethyldisilazide (3.4 mL, 4.4 mmol, 1.3M) with a reaction time of 3 hours at room temperature. The crude product was purified by chromatography (silica gel, 2% ethyl acetate/methylene chloride) to afford 0.78 g (76%) of a mixture of the E and Z isomers as an off white solid: mp 78-82° C.; 1H NMR (CDCl3) δ7.68-7.73 (m, 2 H), 7.16-6.75 (m, 7 H), 6.54-6.39 (m, 3 H), 5.87 (s, 1 H), 5.30 (s, 1 H), 3.93 (s, 3 H), 3.93 (s, 3 H), 3.91 (s, 3 H), 3.88 (s, 3 H); 13C NMR (CDCl3) δ152.0, 150.7, 150.5, 150.4, 149.3, 148.8, 148.7, 148.7, 145.2, 145.0, 129.6, 126.7, 122.1, 121.6, 118.1, 118.0, 116.5, 115.6, 112.5, 112.1, 112.0, 111.5, 110.9, 110.8, 90.5, 90.2, 55.9, 55.9, 55.9, 55.8; Anal. Calcd for C15H13NO3. Theoretical: C, 70.58; H, 5.13; N, 5.49. Found: C, 70.61;H, 5.09; N, 5.18.
Aufarbeitung
- customwith a reaction time of 3 hours
- customat room temperature
- customThe crude product was purified by chromatography (silica gel, 2% ethyl acetate/methylene chloride)
Quellen und Nachweise
- ORD-Eintrag
- ord-95b104aace4e4d548c5839c4a4a05f90
- Quelldatensatz
- uspto-grants-2001_07
- Patentnummer
- US06262101B1
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