Methyl 3-(5-ethyl-2-furyl)propanoate → 5-Ethyl-2-(3-hydroxypropyl)furan
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
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
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.
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-e928cf68874d4371bfd12afee4e6ff02
- Source dataset
- uspto-grants-1996_10
- Patent number
- US05567717
Reaction notes
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