Sodium hydride → HCID 73197847, Verbindung

HRID 2213351Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2213351
[CH3:1][O:2][C:3](=[O:23])[C:4]([C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=1)=[CH:5][C:6]1[CH:11]=[C:10]([O:12][CH3:13])[CH:9]=[C:8]([O:14][CH3:15])[CH:7]=1.[H-].[Na+].F[C:27]1[CH:34]=[CH:33][C:30]([CH:31]=[O:32])=[CH:29][CH:28]=1>CN(C=O)C.C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:23])[C:4]([C:16]1[CH:17]=[CH:18][C:19]([O:22][C:27]2[CH:34]=[CH:33][C:30]([CH:31]=[O:32])=[CH:29][CH:28]=2)=[CH:20][CH:21]=1)=[CH:5][C:6]1[CH:7]=[C:8]([O:14][CH3:15])[CH:9]=[C:10]([O:12][CH3:13])[CH:11]=1

Komponenten

6

Edukt 3

HCID 24758Sodium hydrideHCID 680234-FluorobenzaldehydeHCID 687765982-[4-Hydroxyphenyl]-3-(3,5-dimethoxyphenyl)acrylic acid methyl ester

Produkt 1

HCID 73197847HCID 73197847, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

Under argon, Compound V (433 g, 1.37 mol) was dissolved in dry DMF (1.6 L) and to this sodium hydride (60% in oil, 60.4 g, 1.51 mol) was added. To the resulting orange solution, p-fluorobenzaldehyde (185 mL, 1.71 mol) was added and heated at 80° C. for 18 h. The reaction mixture was cooled to room temperature, diluted with ethyl acetate (3 L) and extracted with water (3 ×1 L), then brine (1×1 L). The organic layer was dried over anhydrous sodium sulfate, filtered and solvent was evaporated. The residue was suspended in methanol (3 L) and stirred overnight. The suspension was chilled and then filtered. Solid obtained was dried under vacuum at 40° C. Yield 445 g (77%). 1HNMR(CDCl3): δ 9.94 (s, 1H), 7.86 (d, J=8.6 Hz, 2H), 7.80 (s, 1H), 7.28J=8.6 Hz, 2H), 7.11(d, J=2.9 Hz, 2H), 7.08(d, J=2.9 Hz, 2H), 6.36(t, J=2.2 Hz, 1H), 6.25 (d, J=2.2 Hz, 2H), 3.83(s, 3H), 3.63 (s, 6H).

Aufarbeitung

  1. additionwas added
  2. temperatureThe reaction mixture was cooled to room temperature
  3. extractionextracted with water (3 ×1 L)
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customsolvent was evaporated
  7. temperatureThe suspension was chilled
  8. filtrationfiltered
  9. customSolid obtained
  10. customwas dried under vacuum at 40° C

Quellen und Nachweise

ORD-Eintrag
ord-e718d5da59004fc898f337ac8674377b
Quelldatensatz
uspto-grants-2006_09
Patentnummer
US07105552B2

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