Acetic Acid → Dimethyl (3,3-dimethyl-2-oxoheptyl)phosphonate
Reaction equation
[CH3:1][P:2](=[O:7])([O:5][CH3:6])[O:3][CH3:4].C([Li])CCC.[CH3:13][C:14]([CH3:24])([CH2:20][CH2:21][CH2:22][CH3:23])[C:15](OCC)=[O:16].C(O)(=O)C>C1COCC1>[CH3:13][C:14]([CH3:24])([CH2:20][CH2:21][CH2:22][CH3:23])[C:15](=[O:16])[CH2:1][P:2](=[O:7])([O:5][CH3:6])[O:3][CH3:4]Participants
6
Conditions
- Temperature
- -78 °C
Procedure
A solution of dimethyl methylphosphonate (35.0 ml) in THF (300 ml) was cooled to -78° C., to which n-butyllithium (1.6-M, 196 ml) was added dropwise. After stirring at -78° C. for one hour, a solution of ethyl 2,2-dimethylcaproate (27 g) in dry THF was added. The reaction solution was stirred at -78° C. for one hour, and then at room temperature for additional 2 hours. The reaction solution was cooled to 0° C. and acetic acid (18 ml) was added thereto. The crude product obtained after the conventional work-up was distilled under reduced pressure and the resulting fraction (>130° C.) was chromatographed to give dimethyl (3,3-dimethyl-2-oxoheptyl)phosphonate. Yield, 9.72 g (26%)
Workup
- additionwas added dropwise
- stirringThe reaction solution was stirred at -78° C. for one hour
- waitat room temperature for additional 2 hours
- temperatureThe reaction solution was cooled to 0° C.
- customThe crude product obtained after the conventional work-up
- distillationwas distilled under reduced pressure
- customthe resulting fraction (>130° C.) was chromatographed
Sources & evidence
- ORD record
- ord-880bf072625541a886a25efd497def86
- Source dataset
- uspto-grants-1997_01
- Patent number
- US05591887
Reaction notes
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