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

HRID 439329

Reaction equation

[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]

Participants

Conditions

Temperature: 0 °C

Procedure

To a mixture of 3.42 g (90.1 mol) 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.

Workup

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)

Sources & evidence

ORD record: ord-2dc55f9da8bd4e42adecbc0ece0f87be
Source dataset: uspto-grants-1996_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05514679

Linked notes

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