Malononitrile → [1-(3-Methoxyphenyl)ethylidene]propanedinitrile
Reaktionsgleichung
C[Si](C)(C)N[Si](C)(C)C.[C:10](#[N:14])[CH2:11][C:12]#[N:13].[CH3:15][C:16]([C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([O:24][CH3:25])[CH:19]=1)=O>C(O)(=O)C>[CH3:25][O:24][C:20]1[CH:19]=[C:18]([C:16](=[C:11]([C:10]#[N:14])[C:12]#[N:13])[CH3:15])[CH:23]=[CH:22][CH:21]=1Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 70 °C
Versuchsvorschrift
To a stirred solution of acetic acid (60 mL) was added hexamethyldisilazane (26.2 mL, 125 mmol) dropwise over 30 min with temperature kept below 40° C. throughout addition. This resulting solution was subsequently added to a stirred solution of malononitrile (13.50 g, 204 mmol) and 3-methoxyacetophenone (13.71 mL, 100 mmol) in acetic acid (30 mL). The final reaction mixture heated to 70° C. under nitrogen for 16 h. The reaction mixture was cooled to RT, partitioned between toluene and water (150 mL each). The aqueous layer was separated and re-extracted with toluene (2×60 mL). The combined organic layer was dried over Na2SO4 and solvent removed in vacuo, to afford the title compound (20 g). LCMS (A) m/z: 199 [M+1]+, Rt 1.20 min (acidic).
Aufarbeitung
- additionkept below 40° C. throughout addition
- customThe final reaction mixture
- temperatureThe reaction mixture was cooled to RT
- custompartitioned between toluene and water (150 mL each)
- customThe aqueous layer was separated
- extractionre-extracted with toluene (2×60 mL)
- dry with materialThe combined organic layer was dried over Na2SO4 and solvent
- customremoved in vacuo
Quellen und Nachweise
- ORD-Eintrag
- ord-57683380c43049ebb8e76570d90c2b9a
- Quelldatensatz
- uspto-grants-2015_05
- Patentnummer
- US09029545B2
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