Acetic Acid → Dimethyl (7-methoxy-2-oxoheptyl)phosphonate
Reaction equation
[CH3:1][P:2](=[O:7])([O:5][CH3:6])[O:3][CH3:4].[CH3:8][O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15](OC)=[O:16].C(O)(=O)C>C1COCC1>[CH3:8][O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15](=[O:16])[CH2:1][P:2](=[O:7])([O:5][CH3:6])[O:3][CH3:4]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -60 °C
Procedure
A solution of dimethyl methylphosphonate (8.88 g) in THF (60 ml) was cooled to -60° C. , to which n-butylithium (1.55-M, 46.2 ml) was added dropwise. After addition, the solution was stirred at -60° C. for 30 minutes. A solution of methyl 6-methoxy-caproate (5.65 g) in THF (50 ml) was added dropwise to the resulting solution and held at -60° C. overnight, and at room temperature for 2 hours. After the reaction solution was cooled to 0° C., the reaction was neutralized by addition of acetic acid (4 ml). The crude product obtained after the usual work-up was chromatographed (dichloromethane/methanol (5%)).
Workup
- additionwas added dropwise
- additionAfter addition
- waitheld at -60° C. overnight
- waitat room temperature for 2 hours
- temperatureAfter the reaction solution was cooled to 0° C.
Sources & evidence
- ORD record
- ord-b375aafb10724bb986b457c61b234137
- Source dataset
- uspto-grants-1992_04
- Patent number
- US05106869
Reaction notes
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