Hydrochloric Acid → Dimethyl(2-oxo-4-phenylbutyl)phosphonate
Reaction equation
[CH3:1][P:2](=[O:7])([O:5][CH3:6])[O:3][CH3:4].C([Li])CCC.CCCCCC.[C:19]1([CH2:25][CH2:26][C:27](OCC)=[O:28])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.Cl>O1CCCC1>[O:28]=[C:27]([CH2:26][CH2:25][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH2:1][P:2](=[O:7])([O:5][CH3:6])[O:3][CH3:4]Participants
Conditions
- Temperature
- -50 °C
Procedure
A solution of dimethyl methylphosphonate (12.4 g., 0.1 mole) in dry tetrahydrofuran (75 ml.) is stirred, maintained under a nitrogen atmosphere, cooled to -50° C., and treated with a 2 N solution of n-butyl lithium in hexane (50 ml., 0.1 mole) added dropwise. Upon completing the addition, the reaction mixture is kept at -50° C. for 1/2 hour to ensure anion formation and then is treated with ethyl 3phenylpropionate (8.9 g., 0.05 mole) added dropwise at -50° C. After stirring for an additional 11/2 hours at -50° to -40° C., the reaction mixture is poured into ice water (250 ml.) providing a turbid solution which is acidified with 2 N hydrochloric acid and extracted with ethyl acetate (4 × 75 ml.). The combined organic extract is dried over sodium sulfate and filtered. Evaporation of the filtrate in vacuo at 40° to 50° C. leaves an oily residue which is distilled to provide the title compound as an oil (11.0 g., 86%), b.p. 148°-150° C./0.1 mm.
Workup
- temperaturemaintained under a nitrogen atmosphere
- additionadded dropwise
- additionthe addition
- additionadded dropwise at -50° C
- customproviding a turbid solution which
- extractionextracted with ethyl acetate (4 × 75 ml.)
- extractionThe combined organic extract
- dry with materialis dried over sodium sulfate
- filtrationfiltered
- customEvaporation of the filtrate in vacuo at 40° to 50° C.
- customleaves an oily residue which
- distillationis distilled
Sources & evidence
- ORD record
- ord-84134ce63d6145ae936c04c65e79f957
- Source dataset
- uspto-grants-1978_07
- Patent number
- US04102888
Reaction notes
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