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[ CAS No. 5006-22-4 ] {[proInfo.proName]}

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Chemical Structure| 5006-22-4
Chemical Structure| 5006-22-4
Structure of 5006-22-4 * Storage: {[proInfo.prStorage]}
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Product Details of [ 5006-22-4 ]

CAS No. :5006-22-4 MDL No. :MFCD00001319
Formula : C5H7ClO Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 118.56 Pubchem ID :-
Synonyms :

Safety of [ 5006-22-4 ]

Signal Word:Danger Class:8,3
Precautionary Statements:P210-P233-P240-P241-P242-P243-P260-P264-P280-P301+P330+P331-P303+P361+P353-P304+P340-P305+P351+P338-P310-P321-P363-P370+P378-P403+P235-P405-P501 UN#:2920
Hazard Statements:H225-H314 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 5006-22-4 ]

* 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.

  • Upstream synthesis route of [ 5006-22-4 ]
  • Downstream synthetic route of [ 5006-22-4 ]

[ 5006-22-4 ] Synthesis Path-Upstream   1~5

  • 1
  • [ 5006-22-4 ]
  • [ 1503-98-6 ]
YieldReaction ConditionsOperation in experiment
71.77% With ammonia In dichloromethane; water at -20 - 20℃; A solution of cyclobutyl carbonyl chloride (5 g, 42.37 mmol) in dichloromethane (20 mL) was treated with aqueous ammonia solution (20 mL) at -20 °C.The resulting reaction mixture was stirred overnight at room temperature. Volatiles were removed under vacuum. The precipitated solid was filtered and dried under vacuum to afford the cyclobutane carboxamide (3 g, 71 .77percent).1H NMR (400 MHz, DMSO-c/6): δ 7.02 - 7.16 (m, 1 H), 6.65 (br. s., 1 H), 2.95 (quind, J=8.43, 8.43, 8.43, 8.43, 0.85 Hz, 1 H), 1 .61 - 2.18 (m, 6H).
71.77% With ammonia In dichloromethane; water at -20 - 20℃; A solution of cyclobutyl carbonyl chloride (5 g, 42.37 mmol) in dichloromethane (20 mL) was treated with aqueous ammonia solution (20 mL) at -20° C. The resulting reaction mixture was stirred overnight at room temperature. Volatiles were removed under vacuum. The precipitated solid was filtered and dried under vacuum to afford the cyclobutane carboxamide (3 g, 71.77percent). 1H NMR (400 MHz, DMSO-d6): δ 7.02-7.16 (m, 1H), 6.65 (br. s., 1H), 2.95 (quind, J=8.43, 8.43, 8.43, 8.43, 0.85 Hz, 1H), 1.61-2.18 (m, 6H).
Reference: [1] Patent: WO2012/160464, 2012, A1, . Location in patent: Page/Page column 60
[2] Patent: US2014/155398, 2014, A1, . Location in patent: Paragraph 0367
[3] Journal of the Chemical Society, 1894, vol. 65, p. 950,969
[4] Journal of Organic Chemistry, 1966, vol. 31, p. 3473 - 3482
[5] Journal of Molecular Structure, 1987, vol. 162, p. 321 - 332
  • 2
  • [ 5006-22-4 ]
  • [ 1503-98-6 ]
Reference: [1] Patent: US5223507, 1993, A,
  • 3
  • [ 5006-22-4 ]
  • [ 6540-33-6 ]
Reference: [1] Molecular Crystals and Liquid Crystals (1969-1991), 1989, vol. 168, p. 229 - 246
  • 4
  • [ 6148-64-7 ]
  • [ 5006-22-4 ]
  • [ 24922-01-8 ]
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
  • 5
  • [ 1071-46-1 ]
  • [ 5006-22-4 ]
  • [ 24922-01-8 ]
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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