Hydrochloric Acid → Dimethyl [2-oxo-3-(pyrid-3-yloxy)propyl]phosphonate
Reaction equation
C([Li])CCC.[CH3:6][P:7](=[O:12])([O:10][CH3:11])[O:8][CH3:9].[N:13]1[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH2:20][C:21](OCC)=[O:22])[CH:14]=1.Cl>CCCCCC.O1CCCC1>[O:22]=[C:21]([CH2:20][O:19][C:15]1[CH:14]=[N:13][CH:18]=[CH:17][CH:16]=1)[CH2:6][P:7](=[O:12])([O:10][CH3:11])[O:8][CH3:9]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- -78 °C
Procedure
n-Butyl-lithium (4.76ml. of a 2.1M solution in hexane) was added to a solution of dimethyl methylphosphonate (1.24g.) in dry tetrahydrofuran at -78° C. in an atmosphere of nitrogen. After 10 minutes, a solution of ethyl 3-pyridyloxyacetate (0.90g.) in dry tetrahydrofuran (5ml.) was added dropwise, and the mixture was stirred for 1 hour at -78° C. The reaction mixture was taken to pH 1-2 with 2N hydrochloric acid and the solvents were removed under reduced pressure. The residue was shaken with water (10ml.) and extracted with ether (3 × 10ml.). The extracts were discarded, and the aqueous solution was adjusted to pH 7-8 with sodium bicarbonate solution and extracted with chloroform (6 × 10ml.). The combined extracts were evaporated, to give dimethyl [2-oxo-3-(pyrid-3-yloxy)propyl]phosphonate as an oil, RF = 0.2 (10% methanol in ethyl acetate).
Workup
- customthe solvents were removed under reduced pressure
- stirringThe residue was shaken with water (10ml.)
- extractionextracted with ether (3 × 10ml.)
- extractionextracted with chloroform (6 × 10ml.)
- customThe combined extracts were evaporated
Sources & evidence
- ORD record
- ord-5e5daa08e9384a8d9045fb63a4cd4afc
- Source dataset
- uspto-grants-1976_12
- Patent number
- US04000305
Reaction notes
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