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[ CAS No. 24922-01-8 ]

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Chemical Structure| 24922-01-8
Chemical Structure| 24922-01-8
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CAS No. :24922-01-8 MDL No. :MFCD06410651
Formula : C9H14O3 Boiling Point : 234.5°C at 760 mmHg
Linear Structure Formula :- InChI Key :N/A
M.W :170.21 g/mol Pubchem ID :21846412
Synonyms :

Safety of [ 24922-01-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 24922-01-8 ]

  • Upstream synthesis route of [ 24922-01-8 ]
  • Downstream synthetic route of [ 24922-01-8 ]

[ 24922-01-8 ] Synthesis Path-Upstream   1~5

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YieldReaction ConditionsOperation in experiment
98%
Stage #1: With triethylamine; magnesium chloride In acetonitrile at 10 - 20℃; for 2.5 h; Inert atmosphere
Stage #2: at 0 - 20℃; for 19 h;
Stage #3: With hydrogenchloride In water; ethyl acetate
The ethyl 3-cyclobutyl-3-oxopropanoate used as starting material was prepared as follows: To a suspension of potassium 3-ethoxy-3-oxopropanoate (60.3 g, 354.25 mmol) in acetonitrile (600 mL) under argon at 10 °C was added triethylamine (75 mL, 540 mmol) then magnesium chloride (40.2 g, 421.72 mmol) keeping the temperature below 25 °C. The thick white suspension was stirred for 2.5 hours under argon at room temperature.Cyclobutanecarbonyl chloride (19.25 mL, 167 mmol) was added slowly (over 1 hour) to the re-cooled mixture at 0-5 °C. The reaction was allowed to warm to room temperature and was stirred for 18 hours. The solvent was then evaporated. The white residue was taken up in EtOAc (700 mL) and 2M HC1 (about 400 mL) was added until it was all in solution (pH of aqueous = 5). The organic layer was separated then washed with 2M. HC1 (200 mL), sat. NaHC03 (2 x 200 mL, saturated aqueous solution) and the organic layer was dried (MgS04), filtered and evaporated to afford ethyl 3-cyclobutyl-3-oxopropanoate(28.0 g, 98 percent) as pale yellow oil.1H NMR (400.132 MHz, CDC13) δ 1.28 (3H, t), 1.80-1.89 (1H, m), 1.91-2.05 (1H, m), 2.12-2.34 (4H, m), 3.39 (2H, s), 3.34-3.42 (1H, m), 4.19 (2H, q).
Reference: [1] Patent: WO2011/114148, 2011, A1, . Location in patent: Page/Page column 81
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YieldReaction ConditionsOperation in experiment
78% With [2,2]bipyridinyl; n-butyllithium In tetrahydrofuran; hexanes at -55 - 20℃; 9a)
Ethyl 3-cyclobutyl-3-oxopropanoate
To a solution of monoethyl malonate (12.0 mL, 101 mmol) and a few milligrams of 2,2'-bipyridyl in tetrahydrofuran (250 mL) at approximately -55° C. was added in a dropwise fashion butyl lithium (2.5 M in hexanes, 81.0 mL, 202 mmol).
Then cyclobutanecarbonyl chloride (6.00 mL, 50.6 mmol) was added dropwise.
The flask was removed from the cold bath and the mixture was allowed to stir while warming to ambient temperature.
The mixture was poured into 1 N aqueous hydrochloric acid and extracted twice with ether.
The combined organic layers were dried over magnesium sulfate, washed twice with saturated sodium bicarbonate, dried again over magnesium sulfate, concentrated and purified by chromatography (silica gel, 7.5percent ethyl acetate in hexanes) to afford ethyl 3-cyclobutyl-3-oxopropanoate (6.69 g, 78percent).
1H-NMR (400 MHz, DMSO-d6) δ 4.06 (q, J=7 Hz, 2H), 3.49 (s, 2H), 3.38-3.32 (m, 1H), 2.11-2.05 (m, 4H), 1.90-1.85 (m, 1H), 1.87-1.66 (m, 1H) 1.15 (t, J=7 Hz, 3H).
Reference: [1] Patent: US2008/96921, 2008, A1, . Location in patent: Page/Page column 45
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Reference: [1] Bioorganic and Medicinal Chemistry, 2017, vol. 25, # 15, p. 3922 - 3946
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Reference: [1] European Journal of Organic Chemistry, 2016, vol. 2016, # 34, p. 5629 - 5632
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Reference: [1] Journal of the American Chemical Society, 1948, vol. 70, p. 497,499
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