Ethanol → HCID 71294206, compound
Reaction equation
[CH3:1][C:2]1[O:6][C:5]([CH:7]=[CH:8][C:9](=[O:17])[CH2:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:4][CH:3]=1.C(O)C.[H][H]>[Ni].O>[CH3:1][C:2]1[O:6][C:5]([CH2:7][CH2:8][C:9](=[O:17])[CH2:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:4][CH:3]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 70 °C
Procedure
For the hydrogenation reaction, 10 g of ethyl 6-(5-methylfuran-2-yl)-4-oxohex-5-enoate, 1 g of 10% wet weight basis Raney Nickel, 100 mL of ethanol, and 5 mL of water were combined in a Parr Bottle. The mixture was pressurized to 50 psi with hydrogen gas and heated to 70° C. The mixture was stirred until hydrogen uptake stopped. The mixture was cooled to ambient temperature, filtered, and washed with ethanol. The filtrate was rotary evaporated to yield ethyl 6-(5-methylfuran-2-yl)-4-oxohexanoate. The ethyl 6-(5-methylfuran-2-yl)-4-oxohexanoate (9.9 g) was then dissolved in hexanes solvent (Aldrich) and dried with sodium sulfate. The solids were filtered, and washed with hexanes. The hexane was combined with the liquid extract and evaporated to an oil. The oil was dissolved in 100 mL isopropyl alcohol (IPA) and added to a Parr bottle containing IPA-washed Raney Nickel (5.0 g wet weight). The reaction mixture was pressurized to 50 psi with hydrogen gas and heated to 70° C. The reaction mixture was stirred until hydrogen uptake stopped. The Raney Nickel was filtered off and washed with IPA. The IPA was then combined with the liquid extract and evaporated to produce ethyl 4-hydroxy-6-(5-methyltetrahydrofuran-2-yl)hexanoate.
Workup
- temperatureThe mixture was cooled to ambient temperature
- filtrationfiltered
- washwashed with ethanol
- customThe filtrate was rotary evaporated
Sources & evidence
- ORD record
- ord-d628cd40c7b34f9698d577a3d13bcdf1
- Source dataset
- uspto-grants-2014_12
- Patent number
- US08901329B2
Reaction notes
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