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[ CAS No. 24922-00-7 ]

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Chemical Structure| 24922-00-7
Chemical Structure| 24922-00-7
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CAS No. :24922-00-7 MDL No. :MFCD06410650
Formula : C10H16O3 Boiling Point : 255.3°C at 760 mmHg
Linear Structure Formula :- InChI Key :-
M.W :184.23 g/mol Pubchem ID :11159709
Synonyms :

Safety of [ 24922-00-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P305+P351+P338 UN#:N/A
Hazard Statements:H227-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 24922-00-7 ]

  • Upstream synthesis route of [ 24922-00-7 ]
  • Downstream synthetic route of [ 24922-00-7 ]

[ 24922-00-7 ] Synthesis Path-Upstream   1~10

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YieldReaction ConditionsOperation in experiment
89%
Stage #1: With [2,2]bipyridinyl; n-butyllithium In hexanes at -65 - -55℃;
Stage #2: at 20℃;
6a)
Ethyl 3-cyclopentyl-3-oxopropanoate
To a solution of monoethyl malonate (13.6 mL, 115 mmol) and a few milligrams of 2,2'-bipyridyl at between -55 and -65° C. was slowly added a 2.4 M solution of n-butyl lithium in hexanes (92.0 mL, 230 mmol).
After the addition was complete, cyclopentanecarbonyl chloride (7.0 mL, 58 mmol) was added in portions.
The solution was then allowed to stir while warming to ambient temperature and was poured into a mix of 1 N aqueous hydrochloric acid and ether.
The layers were separated and the ether layer was washed three times with saturated sodium bicarbonate, dried over magnesium sulfate, concentrated and purified by chromatography (silica gel, 0-5percent ethyl acetate in hexanes gradient elution) to afford ethyl 3-cyclopentyl-3-oxopropanoate (9.50 g, 89percent).
1H-NMR (400 MHz, DMSO-d6) δ 4.06 (q, J=7 Hz, 2H), 3.60 (s, 2H), 2.99-2.91 (m, 1H), 1.78-1.47 (m, 8H), 1.15 (t, J=7 Hz, 3H).
Reference: [1] Patent: US2008/96921, 2008, A1, . Location in patent: Page/Page column 42
[2] Journal of Medicinal Chemistry, 1998, vol. 41, # 17, p. 3186 - 3201
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YieldReaction ConditionsOperation in experiment
77% With triethylamine; magnesium chloride In acetonitrile at 0℃; for 4 h; Potassium monoethyl malonate (20 g, 118 mmol, 2.05 equiv.) is dispersed in anhydrous acetonitrile (200 ml) and magnesium chloride (13.64 g, 143 mmol, 2.5 equiv.) and triethylamine (18.38 ml, 132 mmol, 2.3 equiv.) are added at O °C. After 10 min, cyclopentanecarbonyl chloride (6.97 ml, 57.3 mmol) is added and the orange suspension is stirred at 0 0C. After 4 h, the reaction mixture is concentrated in vacuo and the residue is partitioned between DCM and aqueous 0.5 M KHSO4 solution. The organic layer is washed with aqueous 0.5 M KHSO4 solution and brine, dried over Na2SO4 and concentrated to dryness to afford a brown oil. The oily residue is purified by flash column chromatography (3-30percent EtOAc in heptane) to give 8.12 g (77percent) of the product as an orange oil. 1H-NMR (400 MHz, CDCI3): δ (ppm) 1.28 (3H, t), 1.54-1.73 (4H, m), 1.73-1.90 (4H, m), 2.95-3.04 (1 H, m), 3.49 (2H, s), 4.20 (2H, q).
Reference: [1] Patent: WO2010/139483, 2010, A1, . Location in patent: Page/Page column 67-68
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Reference: [1] Patent: WO2017/60854, 2017, A1, . Location in patent: Page/Page column 156; 157
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Reference: [1] Journal of Organic Chemistry, 1980, vol. 45, # 1, p. 43 - 47
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Reference: [1] Tetrahedron Letters, 2006, vol. 47, # 50, p. 8859 - 8861
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Reference: [1] Journal of the American Chemical Society, 1948, vol. 70, p. 497,499
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  • [ 71911-61-0 ]
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Reference: [1] Journal of Organic Chemistry, 1980, vol. 45, # 1, p. 43 - 47
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  • [ 64-17-5 ]
  • [ 134302-12-8 ]
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Reference: [1] Journal of Medicinal Chemistry, 1998, vol. 41, # 17, p. 3186 - 3201
  • 9
  • [ 105-53-3 ]
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Reference: [1] Journal of Organic Chemistry, 1980, vol. 45, # 1, p. 43 - 47
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  • [ 6004-60-0 ]
  • [ 105-58-8 ]
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Reference: [1] Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1955, vol. 241, p. 602
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