3-Chloro-2-chloromethyl-1-propene → (2-Chloromethyl-2-propenyloxymethyl)phosphonic acid diethylester
Reaction equation
[CH2:1]([O:3][P:4]([CH2:9][OH:10])(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2].[Cl:11][CH2:12][C:13]([CH2:15]Cl)=[CH2:14].[I+].C([N+](CCCC)(CCCC)CCCC)CCC.[Cl-].[NH4+]>O1CCCC1.[H-].[Na+]>[CH2:1]([O:3][P:4]([CH2:9][O:10][CH2:15][C:13]([CH2:12][Cl:11])=[CH2:14])(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 20 °C
Procedure
To a mixture of hydroxymethylphosphonic acid diethylester (0.84 g, 5 mmol), 1-chloro-2-chloromethyl-2-propene (0.95 g, 7.6 mmol) and tetrabutylammonium iodine (0.18 g, 0.5 mmol) in anhydrous tetrahydrofuran (10 ml), sodium hydride is added (0.24 g, 6 mmol 60% in oil) at 0° C. The mixture is stirred overnight at 20° C. The reaction mixture is hydrolyzed with a saturated solution of ammonium chloride, extracted with ethyl acetate and the title product is obtained by flash chromatography on silica gel (0.35 g, 27%).
Workup
- additionis added (0.24 g, 6 mmol 60% in oil) at 0° C
- extractionextracted with ethyl acetate
Sources & evidence
- ORD record
- ord-97609aceb5cf4b4883961a31b3e9b9a7
- Source dataset
- uspto-grants-1999_07
- Patent number
- US05922696
Reaction notes
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