Water → HCID 12387502, Verbindung

HRID 1497004Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1497004
[H-].[Na+].[CH3:3][CH2:4][O:5][C:6]([CH2:8]P(OCC)(OCC)=O)=[O:7].[CH:17](=O)/[CH:18]=[CH:19]/[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26].O>O1CCCC1>[C:6]([O:5][CH2:4][CH3:3])(=[O:7])/[CH:8]=[CH:17]/[CH:18]=[CH:19]/[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]

Komponenten

6

Edukt 4

HCID 962WaterHCID 13345Triethyl phosphonoacetateHCID 24758Sodium hydrideHCID 5283345(2E)-Decenal

Produkt 1

HCID 12387502HCID 12387502, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Sodium hydride (60% wt., 3.11 g) was suspended in dry tetrahydrofuran (200 ml) and cooled to 0° C. O,O-Diethyl ethoxycarbonylmethyl phosphonate (15.43 ml) was added dropwise. The reaction mixture was stirred at 0° C. for 30 min and cooled to −78° C. after which (E)-dec-2-enal (11.90 ml) was added dropwise. Stirring was continued at this temperature for 2 h, after which the mixture was warmed to room temperature. The reaction mixture was poured into water, and the aqueous phase was extracted with ethyl acetate. The combined organic layer was washed with brine, dried over sodium sulfate, and the solvent was evaporated. The crude product was purified by column chromatography.

Aufarbeitung

  1. additionwas added dropwise
  2. stirringStirring
  3. waitwas continued at this temperature for 2 h
  4. temperatureafter which the mixture was warmed to room temperature
  5. extractionthe aqueous phase was extracted with ethyl acetate
  6. washThe combined organic layer was washed with brine
  7. dry with materialdried over sodium sulfate
  8. customthe solvent was evaporated
  9. customThe crude product was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-0bcd2b0918dc493d874f2d18864c700a
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09199948B2

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