Methyl 3-(5-ethyl-2-furyl)propanoate → 5-Ethyl-2-(3-hydroxypropyl)furan

HRID 1377818

Reaktionsgleichung

[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH2:7]([C:9]1[O:13][C:12]([CH2:14][CH2:15][C:16](OC)=[O:17])=[CH:11][CH:10]=1)[CH3:8]>C1COCC1>[CH2:7]([C:9]1[O:13][C:12]([CH2:14][CH2:15][CH2:16][OH:17])=[CH:11][CH:10]=1)[CH3:8]

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

To a mixture of 3.42 g (90.1 mmol) of LAH in THF under nitrogen and stirring at 0° C., was added dropwise 14.9 g (81.9 mmol) of methyl 3-(5-ethyl-2-furyl)propanoate in THF. The reaction mixture was quenched with 3.4 mL of water, 3.4 mL of sodium hydroxide solution, and 10.2 mL of water. Magnesium sulfate was added to the mixture with stirring, filtered and concentrated in vacuo. The residue was passed through silica gel and eluted with ethyl acetate/hexane (2:8) to yield 10.7 g (85%) of the desired product as a clear colorless oil, used in the next preparation without further purification.

Aufarbeitung

customThe reaction mixture was quenched with 3.4 mL of water, 3.4 mL of sodium hydroxide solution, and 10.2 mL of water
additionMagnesium sulfate was added to the mixture
stirringwith stirring
filtrationfiltered
concentrationconcentrated in vacuo
washeluted with ethyl acetate/hexane (2:8)

Quellen und Nachweise

ORD-Eintrag: ord-eee48c12d7f54113ae8ba7adab96bcd8
Quelldatensatz: uspto-grants-1997_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05665763

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