Dimethylformamide → Dimethyl [2-(4-fluoro-2-nitrophenyl)-1-phenylethyl]malonate

HRID 1593274

Reaktionsgleichung

Reaktionsgleichung von HRID 1593274
C1(=O)O[CH:6](C2C=CC=CC=2)[O:5][C:3](=[O:4])C1.[H-].[Na+].[F:17][C:18]1[CH:23]=[CH:22][C:21]([CH3:24])=[C:20]([N+:25]([O-:27])=[O:26])[CH:19]=1.[CH3:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33].[C:34]([O:37][CH2:38]C)(=[O:36])[CH3:35].[CH3:40]N(C=O)C>>[F:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24][CH:40]([CH:35]([C:34]([O:37][CH3:38])=[O:36])[C:3]([O:5][CH3:6])=[O:4])[C:30]2[CH:29]=[CH:28][CH:33]=[CH:32][CH:31]=2)=[C:20]([N+:25]([O-:27])=[O:26])[CH:19]=1

Komponenten

6

Edukt 5

HCID 6228Dimethylformamide2×HCID 24758Sodium hydrideHCID 679654-Fluoro-2-nitrotolueneHCID 9338292-Phenyl-1,3-dioxane-4,6-dioneHCID 21226206Ethyl acetate hexane2×

Produkt 1

HCID 59688514Dimethyl [2-(4-fluoro-2-nitrophenyl)-1-phenylethyl]malonateAusbeute 30 %

Versuchsvorschrift

A solution of benzylidene malonate (14.2 g) in DMF (280 mL) was treated with sodium hydride (2.57 g, 95%). A solution of 4-fluoro-2-nitrotoluene in DMF (10 mL) was added over 1 H, and the reaction mixture was stirred at RT overnight and then quenched by the addition of glacial acetic acid (175 mL) at 0° C. A total of 500 mL of 70:30 water-methanol was added with stirring, and the organics were extracted with ethyl acetate. The organic extracts were combined and washed with saturated aqueous potassium carbonate solution (2×) and brine, dried over sodium sulfate, filtered, and concentrated in vacuo to give a dark brown oil. Flash chromatography on silica gel (75:25 hexane-ethyl acetate, then 50:50 hexane-ethyl acetate) provided 7.0 g (30%) of the title compound as a red-brown solid. 1H NMR (300 MHz, CDCl3) δ 3.72 (d, 2H), 3.73 (d, 1H), 4.32 (m, 1H), 7.09-7.29 (m, 7H), 7.71 (m, 1H). MS APCI, m/z=398 (M+Na). LC/MS: 2.66 min.

Aufarbeitung

  1. customquenched by the addition of glacial acetic acid (175 mL) at 0° C
  2. additionA total of 500 mL of 70:30 water-methanol was added
  3. stirringwith stirring
  4. extractionthe organics were extracted with ethyl acetate
  5. washwashed with saturated aqueous potassium carbonate solution (2×) and brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customto give a dark brown oil

Quellen und Nachweise

ORD-Eintrag
ord-8ce458837bd1412ca08a0bf12831ea4f
Quelldatensatz
uspto-grants-2007_11
Patentnummer
US07294622B2

Verknüpfte Notizen

Wird geladen…