Acetic Acid → Dimethyl(2-oxo-3,6-dimethyl-5-heptenyl)phosphonate
Reaction equation
C([Li])CCC.[CH3:6][O:7][P:8]([CH3:12])(=[O:11])[O:9][CH3:10].C([O:15][C:16](=O)[CH:17]([CH3:23])[CH2:18][CH:19]=[C:20]([CH3:22])[CH3:21])C.C(O)(=O)C>CCCCCC.O1CCCC1>[CH3:6][O:7][P:8]([CH2:12][C:16]([CH:17]([CH3:23])[CH2:18][CH:19]=[C:20]([CH3:22])[CH3:21])=[O:15])(=[O:11])[O:9][CH3:10]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
Under argon at -60° C., 274.7 ml of a 1.61-molar butyllithium solution in hexane was added dropwise to a solution of 59 g of methanephosphonic acid dimethyl ester in 400 ml of absolute tetrahydrofuran. After 15 minutes of agitation, a solution of 34.05 g of 2,5-dimethyl-4-hexenoic acid ethyl ester in 100 ml of absolute tetrahydrofuran was added dropwise thereto. The reaction mixture was allowed to warm up to room temperature within 4 hours and thereafter stirred for another 3 hours. Then the mixture was combined with 26.5 ml of glacial acetic acid and concentrated under vacuum. The residue was taken up in ether/water, the aqueous phase was combined with solid sodium chloride, and shaken out with ether. The combined organic phases were dried over magnesium sulfate and concentrated on a forced circulation evaporator. The evaporation residue was purified by column chromatography on silica gel with hexane/50-100% ethyl acetate as the mobile phase, thus producing 32 g of the desired compound.
Workup
- concentrationconcentrated under vacuum
- stirringshaken out with ether
- dry with materialThe combined organic phases were dried over magnesium sulfate
- concentrationconcentrated on a forced circulation evaporator
- customThe evaporation residue was purified by column chromatography on silica gel with hexane/50-100% ethyl acetate as the mobile phase
Sources & evidence
- ORD record
- ord-539b8c249f144ab09747fe6d9d63905c
- Source dataset
- uspto-grants-1986_01
- Patent number
- US04567195
Reaction notes
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