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Chemical Structure| 1067-74-9 Chemical Structure| 1067-74-9
Chemical Structure| 1067-74-9

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CAS No.: 1067-74-9

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Methyl 2-(diethoxyphosphoryl)acetate is reactant or reagent for synthesis of branches allylic fluorides and regioselective Diels-Alder reactions to yield antibiotic building blocks etc.

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Product Details of Methyl diethylphosphonoacetate

CAS No. :1067-74-9
Formula : C7H15O5P
M.W : 210.16
SMILES Code : O=C(OC)CP(OCC)(OCC)=O
MDL No. :MFCD00009081
InChI Key :CTSAXXHOGZNKJR-UHFFFAOYSA-N
Pubchem ID :66113

Safety of Methyl diethylphosphonoacetate

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319
Precautionary Statements:P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313

Application In Synthesis of Methyl diethylphosphonoacetate

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 1067-74-9 ]

[ 1067-74-9 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 18791-78-1 ]
  • [ 1067-74-9 ]
  • [ 102053-84-9 ]
  • 2
  • [ 1067-74-9 ]
  • [ 145549-76-4 ]
  • C12H18O4 [ No CAS ]
  • 3
  • [ 3314-30-5 ]
  • [ 1067-74-9 ]
  • methyl (2E)-3-(1H-1,3-benzimidazol-2-yl)prop-2-enoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% At room temperature,3.79 g (27.4 mmol) of K2CO3 was placed in 100 mlEggplant bottle,40 ml of dry THF was added,Under stirring, 3.17 g (15 mmol)Phosphonoacetic acidMethyl ester diethyl ester,After stirring at room temperature for 30 min,To the eggplant flask was added 2 g (13.7 mmol)Benzimidazole-2-carbaldehyde,The reaction system was then placed in a N2 atmosphere,66 C for 24 hours.After completion of the reaction, the reaction solution was cooled, filtered, the filtrate was evaporated to dryness,A large amount of ethyl acetate was re-dissolved and then washed three times with saturated NaCl solutionDried over sodium sulfate, filtered and evaporated to dryness to give a yellow solid which was purified by flash chromatography (petroleum ether: ethyl acetate = 4: 1) to give a white solid in 85% to 90% yield.
87.5% To a solution of methyl diethylphosphonoacetate(3.17g, 15.0 mmol) in dry THF (40 mL) was added sodium carbonate (3.79 g, 27.4 mmol), the mixturewas stirred for 30 min at room temperature prior to the addition of compound 2 (2.0 g, 13.7 mmol).The mixture was stirred and refluxed for 24 h under an argon atmosphere and monitored by TLC.After complete conversion of starting material, the reaction mixture was filtered, the filtrate wasconcentrated and re-dissolved by ethyl acetate, and then washed with saturated NaCl solution anddried over anhydrous sodium sulfate, concentrated in vacuo and purified by flash silica gel column(PE/EA = 4/1, v/v) to obtain 3 as white solid in 87.5% yield. LC-MS m/z: 203.1 [M + H]+.
65% With potassium carbonate; In tetrahydrofuran; at 20 - 66℃; for 24.5h; A mixture of methyl phosphonoacetate(7.77 g, 0.037 mmol), potassium carbonate (9.38 g, 0.068 mmol) was dissolved100 mL of tetrahydrofuran, and the mixture was stirred at room temperature for half an hour and then slowly added dropwise to the above tetrahydrofuran solution. The temperature was raised to 66 CStir for 24 hours. After completion of the reaction, filtration was carried out, and most of the tetrahydrofuran was distilled off under reduced pressure. 300 mL of ethyl acetate was added, washed with waterTimes, saturated sodium chloride solution washed once, anhydrous sodium sulfate drying overnight. The solvent was concentrated under reduced pressure and the column chromatography gave pale yellowThe yield was 65%.
 

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