3-Methyl-2-oxohept-5-ynylphosphonic acid dimethyl ester → Dimethyl 2-Oxo-3-methylheptylphosphonate

HRID 867769Notes

Reaction equation

HRID 867769 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

HCID 110426053-Methyl-2-oxohept-5-ynylphosphonic acid dimethyl ester

Product 1

HCID 12906670Dimethyl 2-Oxo-3-methylheptylphosphonateYield 80%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

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.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. distillationThe residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-eb97e57110e344e9ae2136bfc6bc6af4
Source dataset
uspto-grants-1988_10
Patent number
US04775692

Reaction notes

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