Ethyl caprate → 1-Decanol

HRID 1588020Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1588020
CC(C)[O-].[Nd+3].CC(C)[O-].CC(C)[O-].C(O[SiH](OCC)OCC)C.[C:24](OCC)(=[O:34])[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33].[SiH4].[OH-].[Na+]>C1COCC1>[CH2:24]([OH:34])[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33]

Komponenten

7

Edukt 5

HCID 8048Ethyl caprateHCID 13830TriethoxysilaneHCID 14798Sodium HydroxideHCID 23953SilaneHCID 2734134Neodymium(III) isopropoxide

Produkt 1

HCID 81741-DecanolAusbeute 24 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A dry Schlenk tube under argon was charged with 48 mg (0.15 mmol) of neodymium (III) isopropoxide. Triethoxysilane (1.4 mL, 7.5 mmol) and ethyl decanoate (696 μL, 3 mmol) were added and the reaction mixture was heated to 60° C. After 7 hours exposure of the reaction mixture to air caused a flame, presumably due to SiH4 gas evolution. After 29 hours, THF (8 mL) and aqueous NaOH (1 N, 15 mL) were added, and the mixture was stirred vigorously for 2.5 hours. The reaction was worked up as in Example 13. Purification by flash chromatography (ether:hexane=3:7) afforded 114 mg (24% yield) of pure decanol and 263 mg (44% yield) of recovered starting material (both >95% pure by 1H-NMR analysis).

Aufarbeitung

  1. waitAfter 29 hours
  2. customPurification by flash chromatography (ether:hexane=3:7)

Quellen und Nachweise

ORD-Eintrag
ord-82c2c85ec8f54371875643c5f2fbdf37
Quelldatensatz
uspto-grants-1993_06
Patentnummer
US05220020

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