Sodium hydride → Ethyl 2-ethoxy-3-[4-[(2,2-diethoxy)ethoxy]phenyl]-2-propenoate

HRID 432976Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 432976
[H-].[Na+].[CH2:3]([O:5][C:6](=[O:19])[CH2:7][O:8][CH2:9][CH2:10]P(OCC)(OCC)=O)[CH3:4].[CH2:20]([O:22][CH:23]([O:34][CH2:35][CH3:36])[CH2:24][O:25][C:26]1[CH:33]=[CH:32][C:29]([CH:30]=O)=[CH:28][CH:27]=1)[CH3:21]>C1COCC1>[CH2:9]([O:8][C:7](=[CH:30][C:29]1[CH:32]=[CH:33][C:26]([O:25][CH2:24][CH:23]([O:34][CH2:35][CH3:36])[O:22][CH2:20][CH3:21])=[CH:27][CH:28]=1)[C:6]([O:5][CH2:3][CH3:4])=[O:19])[CH3:10]

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 15729465Ethyl (diethoxyphosphoryl)ethoxyacetateHCID 187608894-(2,2-Diethoxyethoxy)benzaldehyde

Produkt 1

HCID 54302220Ethyl 2-ethoxy-3-[4-[(2,2-diethoxy)ethoxy]phenyl]-2-propenoateAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel4×

Reaktionsbedingungen

Temperatur
15 °C

Versuchsvorschrift

To a stirred suspension of sodium hydride (756 mg, 32 mmol, 95%) in dry THF (60 mL) was added a solution of ethyl(diethylphosphono)ethoxyacetate (6.20 g, 23.1 mmol) in THF (20 mL) at 0-5° C. dropwise and stirred for 30 min at 5-25° C. To the reaction mixture was added a solution of 4-[(2,2-diethoxy)ethoxy]benzaldehyde (5.0 g, 21.0 mmol) in THF (10 mL) at 25° C. and stirred further for 30 min. After completion of the reaction (TLC monitored), THF was removed and the resultant residue was diluted with water (100 mL) and extracted with ethyl acetate (3×25 mL). The combined organic extracts were washed with brine, dried over anhydrous Na2SO4 and concentrated to yield the title compound (6.5 g, 88%) as a mixture of E/Z isomers.

Aufarbeitung

  1. stirringstirred further for 30 min
  2. customwas removed
  3. additionthe resultant residue was diluted with water (100 mL)
  4. extractionextracted with ethyl acetate (3×25 mL)
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-a6dc36c3c019443992263c68c99919c2
Quelldatensatz
uspto-grants-2003_12
Patentnummer
US06664411B2

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