Pyridine → (-)-Methyl jasmonate
Reaction equation
[O:1]=[C:2]1[CH2:6][CH2:5][CH:4]([CH2:7][C:8]([OH:10])=[O:9])[CH:3]1[CH2:11][C:12]#[C:13][CH2:14][CH3:15].N1C=CC=C[CH:17]=1>[Pd]>[CH3:15][CH2:14]/[CH:13]=[CH:12]\[CH2:11][C@H:3]1[C:2](=[O:1])[CH2:6][CH2:5][C@@H:4]1[CH2:7][C:8]([O:10][CH3:17])=[O:9]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Four hundred mg. of the methyl ester of 3-oxo-2-(2-pentynyl)-cyclopentaneacetic acid dissolved in 10 ml. of pyridine is added to 100 mg of 5% palladium on barium sulfate, and the resulting mixture is hydrogenated at room temperature and pressure. Forty-four milliliters of hydrogen is absorbed in 90 minutes, then the reaction stops completely. After filtering off the catalyst, the solvent is evaporated. The remaining oil is dissolved in ether-hexane 1:1 and washed with 1N HCl, aqueous saturated sodium bicarbonate and finally water. After drying (MgSO4), the solvent is evaporated and 392 mg. of methyl cis-jasmonate is obtained. Yield 98%. Spectral properties are in agreement with the above structure and published spectral data. The product shows one spot on thin layer chromatography. Methyl cis-jasmonate was also characterized as its semicarbazone, m.p. 118°-119° C (Lit. 115°-117° C).
Workup
- customis hydrogenated at room temperature
- customForty-four milliliters of hydrogen is absorbed in 90 minutes
- filtrationAfter filtering off the catalyst
- customthe solvent is evaporated
- dissolutionThe remaining oil is dissolved in ether-hexane 1:1
- washwashed with 1N HCl, aqueous saturated sodium bicarbonate and finally water
- dry with materialAfter drying (MgSO4)
- customthe solvent is evaporated
Sources & evidence
- ORD record
- ord-f9ec25c0ab7744ceba364302c90a7504
- Source dataset
- uspto-grants-1977_03
- Patent number
- US04014919
Reaction notes
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