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[ CAS No. 29668-62-0 ] {[proInfo.proName]}

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Chemical Structure| 29668-62-0
Chemical Structure| 29668-62-0
Structure of 29668-62-0 * Storage: {[proInfo.prStorage]}
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Product Details of [ 29668-62-0 ]

CAS No. :29668-62-0 MDL No. :MFCD00015673
Formula : C8H17O5P Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 224.19 Pubchem ID :-
Synonyms :

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Application In Synthesis of [ 29668-62-0 ]

* 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 [ 29668-62-0 ]

[ 29668-62-0 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 5445-17-0 ]
  • [ 122-52-1 ]
  • [ 29668-62-0 ]
YieldReaction ConditionsOperation in experiment
100% In neat (no solvent); at 110℃; Methyl 2-bromopropanoate (1.0 eq, 10 g, 59.9 mmol) and triethylphosphite (5.0 eq, 299.5 mmol, 51.5 mL) were combined neat and heated to 110 C. with stirring overnight. The reaction mixture was concentrated, azeotroped with toluene 3×, and dried under high vacuum. The resulting phosphonate was obtained in quantitative yield and was used directly in the following reaction: The phosphonate (1.0 eq, 10.0 g, 44.6 mmol) was dissolved in anhydrous THF (100 mL) and cooled to 0 C. To this mixture, n-BuLi (2.5 M in Hexanes, 18.7 mL, 46.8 mmol, 1.05 eq) was added drop wise. The mixture was stirred for 2 hours at 0 C., then cyclohexanone (1.0 eq, 44.6 mmol, 4.6 mL) was added. The mixture was stirred at 0 C. gradually warming to ambient temperature over 72 hours. The reaction was quenched with saturated aqueous ammonium chloride (500 mL) and concentrated. The remaining aqueous layer was extracted with ethyl acetate (2×200 mL) to give 16.8 g of the crude ester as a yellow oil which was purified by flash column chromatography (hex/ethyl acetate gradient). 3.7 g of a pale yellow oil was obtained as mixture of methyl and ethyl esters in about 1.4:1 molar ratio (21.25 mmol, 48% yield). The isolated mixed ester (3.2 g, 18.36 mmol) was dissolved in ethanol (50 mL) and solid sodium hydroxide (1.0 g, 25 mmol) was added. The mixture was refluxed until reaction was complete. Ethanol was subsequently removed and the residue was partitioned between ethyl acetate (50 mL) and a 1.0 N solution of HCl (50 mL). The aqueous layer was acidified with 6.0 N HCl until acidic and extracted with ethyl acetate (50 mL) again. Combined organic layers were washed with brine and dried over magnesium sulfate. The crude material was purified by flash column chromatography (hex/ethyl acetate gradient) to afford 2.0 g (71% yield) of the desired isomer as a yellow oil in 90% purity by 1H-NMR. (0850) 1H NMR (400 MHz, DMSO-d6): delta, ppm: 12.18 (s, 1H), 2.40 (m, 2H), 2.17 (m, 2H), 1.77 (s, 3H), 1.52 (m, 6H).
at 110℃; for 48h; <strong>[5445-17-0]Methyl 2-bromopropionate</strong> (100 g, 0.60 mol) and triethylphosphite (109 g, 0.66 mol) were mixed, and the mixture was stirred at 110C for 2 days. The reaction mixture wasdried under reduced pressure to give the title compound.
at 110℃; for 48h; Step 1. Synthesis of 2-(diethylphosphono)propanoic acid methyl ester <strong>[5445-17-0]Methyl 2-bromopropionate</strong> (100 g, 0.60 mol) and triethylphosphite (109 g, 0.66 mol) were mixed, and the mixture was stirred at 110 C. for 2 days. The reaction mixture was dried under reduced pressure to give the title compound.
  • 2
  • [ 2591-98-2 ]
  • [ 29668-62-0 ]
  • [ 132922-38-4 ]
  • 3
  • [ 29668-62-0 ]
  • [ 3453-33-6 ]
  • 3-(6-methoxynaphthalen-2-yl)-2-methylacrylic acid methyl ester [ No CAS ]
  • 4
  • [ 29668-62-0 ]
  • [ 1504-74-1 ]
  • C14H16O3 [ No CAS ]
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