Hydrochloric Acid → 27238-13-7
Reaction equation
[C:1]([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(P(N(C)C)(N(C)C)=O)C.[P:26](Cl)([O:31][CH2:32][CH3:33])([O:28][CH2:29][CH3:30])=[O:27].Cl>CN(C1C=CN=CC=1)C.CCOCC>[CH2:13]([O:12][C:10](=[O:11])/[CH:9]=[C:1](/[O:8][P:26]([O:31][CH2:32][CH3:33])([O:28][CH2:29][CH3:30])=[O:27])\[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH3:14]Participants
Conditions
- Temperature
- 0 °C
Procedure
To a solution of ethyl benzoylacetate (10 g, 52.03 mmol) was added DMAP (699.2 mg, 5.72 mmol), HMPA (9.96 mL, 57.23 mmol), TEA (7.98 mL, 57.23 mmol). The resulting yellow solution was stirred at 0° C. for 30 minutes and then coiled to −20° C. Diethyl chlorophosphate was added dropwise to the cooled solution and a heavy precipitate began to form immediately. The yellow-orange paste was warmed to room temperature and stirred for another 4 hours. The reaction mixture was diluted with ether and acidified with 1N HCl. The ethereal extracts were washed with saturated aqueous CuSO4 to remove HMPA, dried over MgSO4, and concentrated. The residue was purified through flash column chromatography on silica gel (EtOAc:hexanes=2:3) to give 11.6 g in 68% yield.
Workup
- customcoiled to −20° C
- customto form immediately
- temperatureThe yellow-orange paste was warmed to room temperature
- stirringstirred for another 4 hours
- washThe ethereal extracts were washed with saturated aqueous CuSO4
- customto remove HMPA
- dry with materialdried over MgSO4
- concentrationconcentrated
- customThe residue was purified through flash column chromatography on silica gel (EtOAc:hexanes=2:3)
- customto give 11.6 g in 68% yield
Sources & evidence
- ORD record
- ord-8aded512de9e4edc8c09e380821c3eed
- Source dataset
- uspto-grants-2007_10
- Patent number
- US07276531B2
Reaction notes
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