Reaction equation
[CH3:1][CH2:2]/[CH:3]=[CH:4]\[CH2:5][C@H:6]1[C:10](=[O:11])[CH2:9][CH2:8][C@@H:7]1[CH2:12][C:13](O)=[O:14].[H-].[Al+3].[Li+].[H-].[H-].[H-].O>O1CCCC1>[CH2:5]([C@H:6]1[CH:10]([OH:11])[CH2:9][CH2:8][C@@H:7]1[CH2:12][CH2:13][OH:14])/[CH:4]=[CH:3]\[CH2:2][CH3:1]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
In a 50 ml three-necked flask equipped with a condenser, a thermometer and a magnetic stirrer, 1 g (4.5 mmol) of methyl (+/−)-jasmonate was dissolved in 15 ml of tetrahydrofuran. 430 mg (11.3 mmol) of lithium aluminium hydride, LiAlH4, were added. The mixture was stirred at 50° C. for 4 hours. When the reaction was finished, 5 ml of water were added slowly. The precipitate formed was filtered off and the filtrate was acidified to pH=5 with hydrochloric acid and then extracted with ethyl acetate (3×30 ml). The organic phase was dried over sodium sulphate, filtered on filter paper, and then concentrated. The colourless oil obtained was purified by chromatography on silica gel (eluent: dichloromethane/methanol). The colourless oil obtained was dried under vacuum.
Workup
- customIn a 50 ml three-necked flask equipped with a condenser
- customThe precipitate formed
- filtrationwas filtered off
- extractionextracted with ethyl acetate (3×30 ml)
- dry with materialThe organic phase was dried over sodium sulphate
- filtrationfiltered
- filtrationon filter paper
- concentrationconcentrated
- customThe colourless oil obtained
- customwas purified by chromatography on silica gel (eluent: dichloromethane/methanol)
- customThe colourless oil obtained
- customwas dried under vacuum
Sources & evidence
- ORD record
- ord-539094d08cc342beb32ea5a5bafcffc1
- Source dataset
- uspto-grants-2013_07
- Patent number
- US08481594B2
Linked notes
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