Water → HCID 24886486, compound
Reaction equation
[CH3:1][CH2:2]/[CH:3]=[CH:4]\[CH2:5][CH:6]1[C:10](=[O:11])[CH2:9][CH2:8][CH:7]1[CH2:12][C:13]([OH:15])=[O:14].O>C(O)C>[OH:11][CH:10]1[CH2:9][CH2:8][C@H:7]([CH2:12][C:13]([OH:15])=[O:14])[C@H:6]1[CH2:5]/[CH:4]=[CH:3]\[CH2:2][CH3:1]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
In a 50 ml three-necked flask equipped with a refrigerant, a thermometer and a magnetic stirring device, 1 g (4.8 mmol) of (+/−)-jasmonic acid (b) was dissolved in 15 ml of absolute ethanol. 430 mg (11.4 mmol) of sodium borohydride NaBH4 was added. The mixture was stirred for 4 hours at 50° C. Once the reaction had ended, 5 ml of water was slowly added. The precipitate formed was filtered off. The filtrate was acidified to a pH=5 with hydrochloric acid and was then extracted with ethyl acetate (3×30 ml). The organic phase was dried over sodium sulphate, filtered through filter paper, and then concentrated. The colorless oil obtained was purified by silica gel chromatography (eluent: dichloromethane/methanol). The colorless oil obtained was dried under vacuum.
Workup
- customIn a 50 ml three-necked flask equipped with a refrigerant
- customThe precipitate formed
- filtrationwas filtered off
- extractionwas then extracted with ethyl acetate (3×30 ml)
- dry with materialThe organic phase was dried over sodium sulphate
- filtrationfiltered
- filtrationthrough filter paper
- concentrationconcentrated
- customThe colorless oil obtained
- customwas purified by silica gel chromatography (eluent: dichloromethane/methanol)
- customThe colorless oil obtained
- customwas dried under vacuum
Sources & evidence
- ORD record
- ord-083e06e9a5154e7e987edf9137771687
- Source dataset
- uspto-grants-2013_06
- Patent number
- US08461206B2
Reaction notes
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