Acetic Acid → Dimethyl 2-Oxo-3-methylheptylphosphonate
Reaction equation
[CH2:1]1[CH2:5][O:4][CH2:3][CH2:2]1.[CH3:6][P:7](=[O:12])([O:10][CH3:11])[O:8][CH3:9].[CH2:13]([Li])[CH2:14]CC.[C:18](O)(=O)C>>[CH3:18][CH:1]([CH2:2][CH2:3][CH2:13][CH3:14])[C:5](=[O:4])[CH2:6][P:7](=[O:12])([O:10][CH3:11])[O:8][CH3:9]Participants
5
Procedure
To a THF (120 ml) solution of dimethyl methylphosphonate (5.04 g) at -60° C. was added dropwise n-BuLi (1.6-M, 25.4 ml), and the mixture was stirred for 30 min. A THF (50 ml) solution of methyl 2R,S-methylcaproate (3 15 g) was added dropwise. The mixture was stirred at -60° C. for 1 h, then at room temperature for 1.5 h, and thereafter acetic acid (2 ml) was added at 0° C. A crude product obtained after the usual work-up was chromatographed (hexane : ethyl acetate=1 : 5). Yield : 2,85 g (58%).
Workup
- stirringThe mixture was stirred at -60° C. for 1 h
- waitat room temperature for 1.5 h
Sources & evidence
- ORD record
- ord-55ad27566e2d406cae1d0bc2d573e2df
- Source dataset
- uspto-grants-1992_11
- Patent number
- US05166174
Reaction notes
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