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Chemical Structure| 62088-13-5 Chemical Structure| 62088-13-5

Structure of 62088-13-5

Chemical Structure| 62088-13-5

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Product Details of [ 62088-13-5 ]

CAS No. :62088-13-5
Formula : C12H11NO3
M.W : 217.22
SMILES Code : CCOC(=O)CC(=O)C1=CC(=CC=C1)C#N
MDL No. :MFCD06656737
InChI Key :BKFPVHXPYUFQHT-UHFFFAOYSA-N
Pubchem ID :11622629

Safety of [ 62088-13-5 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302
Precautionary Statements:P280-P305+P351+P338

Application In Synthesis of [ 62088-13-5 ]

* 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 [ 62088-13-5 ]
  • Downstream synthetic route of [ 62088-13-5 ]

[ 62088-13-5 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 6136-68-1 ]
  • [ 105-58-8 ]
  • [ 62088-13-5 ]
YieldReaction ConditionsOperation in experiment
96% With hydrogenchloride In tetrahydrofuran; mineral oil Part A.
Preparation of ethyl 3-(3-cyanophenyl)-3-oxopropionate.
To a suspension of sodium hydride (1.2 g of 60percent suspension in mineral oil, hexane-washed, 30.3 mmol) in 40 mL of tetrahydrofuran was added diethyl carbonate (3.7 mL, 30.3 mmol) and 3-acetyl benzonitrile (2.2 g, 15.2 mmol).
The resulting suspension was stirred at 65° C for 1 h and then was cooled to room temperature.
There was added 40 mL of 10percent aqueous HCl and the reaction mixture was diluted with ethyl acetate and the layers were separated.
The organic layer was washed with brine, dried (MgSO4) and concentrated in vacuo to afford 3.2 g (96percent) of the title compound, which was sufficiently pure to be used without purification. MS (NH3-CI) 218.3 (M+H)+.
96% With hydrogenchloride In tetrahydrofuran; mineral oil Part A.
Preparation of ethyl 3-(3-cyanophenyl)-3-oxopropionate.
To a suspension of sodium hydride (1.2 g of 60percent suspension in mineral oil, hexane-washed, 30.3 mmol) in 40 mL of tetrahydrofuran was added diethyl carbonate (3.7 mL, 30.3 mmol) and 3-acetyl benzonitrile (2.2 g, 15.2 mmol).
The resulting suspension was stirred at 65° C. for 1 h and then was cooled to room temperature.
There was added 40 mL of 10percent aqueous HCl and the reaction mixture was diluted with ethyl acetate and the layers were separated.
The organic layer was washed with brine, dried (MgSO4) and concentrated in vacuo to afford 3.2 g (96percent) of the title compound, which was sufficiently pure to be used without purification. MS (NH3-CI) 218.3 (M+H)+.
References: [1] Journal of Medicinal Chemistry, 2006, vol. 49, # 6, p. 1910 - 1915.
[2] Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 5, p. 641 - 645.
[3] Patent: WO2011/46774, 2011, A1, . Location in patent: Page/Page column 16.
[4] Patent: EP946528, 2003, B1, .
[5] Patent: US6187797, 2001, B1, .
  • 2
  • [ 15226-74-1 ]
  • [ 6952-59-6 ]
  • [ 6148-64-7 ]
  • [ 62088-13-5 ]
YieldReaction ConditionsOperation in experiment
60% With 1H-imidazole; palladium diacetate; triethylamine; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; magnesium chloride In tetrahydrofuran at 90℃; for 0.5 h; Microwave irradiation To a stirred mixture of aryl or heteroaryl halide(Br, I) (0.5 mmol), potassium mono ethyl malonate (0.75 mmol) in THF (10 mL) taken in a 30 mL microwave vial, was added Pd(OAc)2(5 molpercent), Xantphos (5 mol percent), MgCl2 (0.75), Et3N ( 0.75mmol), imidazole (1 mmol) followed by Co2(CO)8 (0.15mmol). The vial was sealed immediately and microwave irradiated at 90°C for 30min. The reaction mixture was concentrated and diluted with ethyl acetate and water. The ethyl acetate layer was separated, dried over sodium sulphate and concentrated. The crude product obtained was purified by column chromatography to get the pure compound.
References: [1] Tetrahedron Letters, 2014, vol. 55, # 25, p. 3525 - 3528.
 

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