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Chemistry
Heterocyclic Building Blocks
Pyridines
Methyl 2-(4,6-dimethylpyridin-2-yl)acetate
Chemistry
Heterocyclic Building Blocks
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[ CAS No. 58532-57-3 ] {[proInfo.proName]}

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Chemical Structure| 58532-57-3
Chemical Structure| 58532-57-3
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Product Details of [ 58532-57-3 ]

CAS No. :58532-57-3 MDL No. :MFCD18088992
Formula : C10H13NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 179.22 Pubchem ID :-
Synonyms :

Safety of [ 58532-57-3 ]

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Precautionary Statements: UN#:
Hazard Statements: Packing Group:

Application In Synthesis of [ 58532-57-3 ]

* 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 [ 58532-57-3 ]

[ 58532-57-3 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 108-75-8 ]
  • [ 616-38-6 ]
  • [ 58532-57-3 ]
YieldReaction ConditionsOperation in experiment
81% 2,4,6-Trimethylpyridine (1.00 g, 8.25 mmol) was dissolved in tetrahydrofuran (30 mL), lithium diisopropylamide (8.2 mL, 2 M tetrahydrofuran solution, 16.5 mmol) was added at 0C under nitrogen atmosphere. The reaction solution was stirred at 0C for 0.5 hour. Dimethyl carbonate (743 mg, 8.25 mmol) was added to the reaction mixture and then slowly heated to 20C. The stirring was continued for 2 hours. The reaction solution was quenched by the addition of saturated ammonium chloride solution (100 mL). The mixture was extracted with ethyl acetate (20 mL x 3). The organic phase was washed with brine (20 mL x 3), dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (2:1 petroleum ether / ethyl acetate, Rf = 0.5) to give methyl 2-(4,6-dimethylpyridin-2-yl)acetate (1.20 g, as a yellow oil) with a yield of 81%. 1H NMR: (400 MHz, CDCl3) delta 6.91(s, 1H), 6.87(s, 1H), 3.77(s, 2H), 3.70(s, 3H), 2.48(s, 3H), 2.28(s, 3H). MS-ESI calcd. [M + H]+ 180, found 180.
Reference： [1]Patent: EP3299371,2018,A1 .Location in patent: Paragraph 0347; 0348; 0349
[2]Journal of the American Chemical Society,2010,vol. 132,p. 14391 - 14393
  • 2
  • [ 58532-57-3 ]
  • [ 13287-63-3 ]
YieldReaction ConditionsOperation in experiment
92% With lithium aluminium tetrahydride; In tetrahydrofuran; at 0℃; for 1.0h; Methyl 2-(4,6-dimethylpyridin-2-yl)acetate (500 mg, 2.79 mmol) was dissolved in tetrahydrofuran (20 mL), lithium aluminum hydride (211 mg, 5.58 mmol) was added at 0C and reacted for 1 hour. The reaction was quenched by adding water (10 mL), extracted with ethyl acetate (20 mL x 3), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (2:1 petroleum ether / ethyl acetate, Rf = 0.3) to give 2-(4,6-dimethylpyridin-2-yl)ethanol (410 mg, as a yellow oil) with a yield of 92%. MS-ESI calcd. [M + H]+ 152, found 152.
Reference： [1]Patent: EP3299371,2018,A1 .Location in patent: Paragraph 0347; 0350; 0351

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