Water → ethyl (E)-3-(5-ethyl-3-methoxy-4-methoxymethoxy-1-naphthyl)-2-methylpropenoate

HRID 654704Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 654704
[H-].[Na+].[CH3:3][CH2:4][O:5][C:6]([CH:8](P(OCC)(OCC)=O)[CH3:9])=[O:7].[CH2:18]([C:20]1[CH:29]=[CH:28][CH:27]=[C:26]2[C:21]=1[C:22]([O:34][CH2:35][O:36][CH3:37])=[C:23]([O:32][CH3:33])[CH:24]=[C:25]2[CH:30]=O)[CH3:19].O>CN(C)C=O>[CH2:18]([C:20]1[CH:29]=[CH:28][CH:27]=[C:26]2[C:21]=1[C:22]([O:34][CH2:35][O:36][CH3:37])=[C:23]([O:32][CH3:33])[CH:24]=[C:25]2/[CH:30]=[C:8](\[CH3:9])/[C:6]([O:5][CH2:4][CH3:3])=[O:7])[CH3:19]

Komponenten

6

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 107155Triethyl 2-phosphonopropionateHCID 99705695-Ethyl-3-methoxy-4-methoxymethoxy-1-naphthalenecarbaldehyde

Produkt 1

HCID 9975669ethyl (E)-3-(5-ethyl-3-methoxy-4-methoxymethoxy-1-naphthyl)-2-methylpropenoateAusbeute 97,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

36 g of 60% sodium hydride was suspended in 500 ml of N,N-dimethylformamide and 268 g of triethyl 2-phosphonopropionate was added at ice bath temperature. After stirring at room temperature for 1 hour, a solution of 206 g of 5-ethyl-3-methoxy-4-methoxymethoxy-1-naphthalenecarbaldehyde was added. After stirring at room temperature for 15 minutes, ice cooled water was gradually added at ice bath temperature. The mixture was extracted with ethyl acetate and the combined organic layer was washed with brine. After drying over anhydrous magnesium sulfate, the solvent was evaporated and the residue was purified by silica gel column chromatography (10% ethyl acetate/hexane) to obtain 262.4 g of the titled compound as a yellow oil (containing a small amount of Z isomer).

Aufarbeitung

  1. stirringAfter stirring at room temperature for 15 minutes
  2. additionwas gradually added at ice bath temperature
  3. extractionThe mixture was extracted with ethyl acetate
  4. washthe combined organic layer was washed with brine
  5. dry with materialAfter drying over anhydrous magnesium sulfate
  6. customthe solvent was evaporated
  7. customthe residue was purified by silica gel column chromatography (10% ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-ec01aa74e4ed41ca9dc3719d913c064f
Quelldatensatz
uspto-grants-1992_07
Patentnummer
US05134111

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