3-Methyl-2-oxohept-5-ynylphosphonic acid dimethyl ester → Dimethyl 2-Oxo-3-methylheptylphosphonate
Reaction equation
[CH3:1][CH:2]([CH2:12][C:13]#[C:14][CH3:15])[C:3](=[O:11])[CH2:4][P:5](=[O:10])([O:8][CH3:9])[O:6][CH3:7]>C(OCC)(=O)C.[Pd]>[CH3:1][CH:2]([CH2:12][CH2:13][CH2:14][CH3:15])[C:3](=[O:11])[CH2:4][P:5](=[O:10])([O:6][CH3:7])[O:8][CH3:9]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of dimethyl 3-methyl-2-oxo-5-heptynylphosphonate (10.0 g, 0.043 mol) in ethyl acetate (100 ml) was added 10% palladium on active carbon (5.0 g) and the mixture was stirred under hydrogen atmosphere for one hour. The reaction mixture was filtered and the filtrate was concentrated. The residue was distilled under reduced pressure to give colorless oily product dimethyl 3-methyl-2-oxo-heptylphosphonate (8.12 g, 0.034 mol, 80%, b.p. 90°-92° C./0.05 mmHg). The structure was identified by the following data.