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Chemical Structure| 40307-11-7 Chemical Structure| 40307-11-7
Chemical Structure| 40307-11-7

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Krzysztof Kuciński ; Grzegorz Hreczycho ;

Abstract: Commercially available and inexpensive potassium bis(trimethylsilyl)amide (KHMDS) serves as an efficient transition metal-free catalyst for the catalytic sp C−H silylation of several terminal alkynes including two pharmaceuticals. Overall, the presented system allows the synthesis of various attractive silylacetylenes under mild conditions, making this approach an environmentally benign and sustainable alternative to existing synthetic solutions.

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Product Details of 1-Ethyl-4-ethynylbenzene

CAS No. :40307-11-7
Formula : C10H10
M.W : 130.19
SMILES Code : C#CC1=CC=C(CC)C=C1
MDL No. :MFCD00173887
InChI Key :ZNTJVJSUNSUMPP-UHFFFAOYSA-N
Pubchem ID :142425

Safety of 1-Ethyl-4-ethynylbenzene

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of 1-Ethyl-4-ethynylbenzene

* 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 [ 40307-11-7 ]

[ 40307-11-7 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 40307-11-7 ]
  • [ 175278-00-9 ]
  • C17H13F3O [ No CAS ]
  • 2
  • [ 40307-11-7 ]
  • [ 2632-14-6 ]
  • 3
  • [ 40307-11-7 ]
  • [ 163622-50-2 ]
  • C16H14N4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); In tetrahydrofuran; at 120℃; for 0.5h;Microwave irradiation; Inert atmosphere; General procedure: Compound 6 (3.85 mmol), Pd(PPh3)4 (0.077 mmol), CuI (0.77 mmol), AmberliteIR-67, ethynylbenzene or 4-ethylphenylacetylene (4.6 mmol) in 30 mL of THF was heated for 30 min at 120 C in the microwave. After cooling to ambient temperature, the reaction mixture was filtered through a pad of Celite. The solvent was removed in vacuo, and the crude product was purified by flash column chromatography on silica gel (DCM/MeOH= 30/1) to give compound 7i or 7ii as a yellow solid.19 To a solution of 7i or 7ii (7.16 mmol) in DMF (20 mL) was added potassium carbonate (8.6 mmol) followed by 4-bromo-1-butene (8.6 mmol). After stirring at 30 C for 6 h, EtOAc (300 mL) was then added and the solution was washed three times with water. The combined organic phase was dried over Na2SO4 and concentrated. The residue was subjected to column chromatography on silica gel (DCM/MeOH= 30:1) to give compound 8i (83%) or 8ii (~56% yield over two steps). For 8i: Yellow solid; 1H NMR (300 MHz, CDCl3) delta 8.31 (s, 1H), 7.51 - 7.49 (m, 2H), 7.43 - 7.33 (m, 3H), 7.22 (s, 1H), 5.90 (s, 2H), 5.79 - 5.72 (m, 1H), 5.08 (t, J = 16.2, 10.8 Hz, 2H), 4.26 (t, J = 7.2 Hz, 2H), 2.60 (q, J = 6.9 Hz, 2H); For 8ii: Yellow solid; 1H NMR (300 MHz, CDCl3) delta 8.31 (s, 1H), 7.43 (d, J = 7.8 Hz, 2H), 7.20 - 7.18 (m, 3H), 5.92 (s, 2H), 5.82 - 5.73 (m, 1H), 5.17 (t, J =17.1, 9.9 Hz, 2H), 4.24 (t, J = 6.9 Hz, 2H), 2.75 - 2.52 (m, 4H), 1.24 (t, J = 7.5 Hz, 3H).
  • 4
  • [ 40263-57-8 ]
  • [ 40307-11-7 ]
  • 2-(4-ethylphenyl)furo[2,3-b]pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
58% With potassium phosphate; C43H36N4O4Pd; In dimethylsulfoxide-d6; at 120℃; for 10h; General procedure: In a typical run, performed in air, a 25 mL of round bottom askwas charged with a mixture of 2-iodophenol (0.50 mmol), terminalalkyne (0.60 mmol), and K3PO4 (1.00 mmol). A palladium complex(2a or 2b, 0.0005 mmol) was added to the mixture, followed byDMSO (ca. 2 mL) as a solvent, and then the reaction mixture washeated (either at 90C or at 120C) for 10 h. The reaction mixturewas cooled to room temperature, and water (ca. 20 mL) was added.The resulting mixture was extracted with EtOAc (ca. 50 mL). Theorganic layer was further extracted with EtOAc (ca. 2 20 mL). Theorganic layers were combined and vacuum dried to obtain a crudeproduct that was subsequently puried by column chromatog-raphy. The obtained benzofuran derivatives (3aa3ap) were char-acterized by NMR and Mass spectroscopy (See SupportingInformation Figures S4-S23).
 

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