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Chemical Structure| 16238-12-3 Chemical Structure| 16238-12-3

Structure of 16238-12-3

Chemical Structure| 16238-12-3

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Product Details of [ 16238-12-3 ]

CAS No. :16238-12-3
Formula : C10H7NO
M.W : 157.17
SMILES Code : N#CC1=CC=C(OC(C)=C2)C2=C1
MDL No. :MFCD15143966

Safety of [ 16238-12-3 ]

Application In Synthesis of [ 16238-12-3 ]

* 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 [ 16238-12-3 ]

[ 16238-12-3 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 2296-23-3 ]
  • [ 16466-97-0 ]
  • [ 16238-12-3 ]
YieldReaction ConditionsOperation in experiment
2-lodo-4-cynophenol (0.25 g, 1 mmol) and saccharin (0.1 g) in HMDSA (2 ml) was refluxed for 2 h under N2, until the solution became clear. The solvent was distilled off under reduced pressure and the residue was dissolved in anhydrous THF (2 ml). This was added to a solution made by mixing anhydrous ZnCI2 (0.3 g; 2.2 mmol) with 0.5 M 1 -propynyl magnesium bromide in THF (7.8 ml) in anhydrous THF (5 ml) at room temperature under N2 To it, Pd (PPh3)4 (0.15 g) was added at room temperature under N2 followed by catalytic amount of CuI. The mixture was stirred at room temperature for 3 h and quenched with saturated NH4CI solution. The mixture was diluted to 50 ml with EtOAc and washed with H2O. The organic layer was separated, dried over MgSO4 and filtered. The filtrate was evaporated and the residue was dissolved in 1 ,4-dioxane (4 ml) and 1 M TBAF in THF (0.3 ml) was added and this was stirred for 4 h at reflux. The solvent was distilled off and the residue was purified by FCC (SiO2, hexane/EtOAc) to give the title compound (0.145 g, 91 %), as colourless solid. 1H-NMR (CDCI3) 7.78 (s, 1 H); 7.46 - 7.44 (m, 2H); 6.41 (bs, 1 H); 2.47 (s, 3H).
  • 2
  • [ 2296-23-3 ]
  • [ 74-99-7 ]
  • [ 16238-12-3 ]
YieldReaction ConditionsOperation in experiment
91% 2-iodo-4-cynophenol (0.25 g, 1 mmol) was added hexamethyldisilazine (2 ml) and saccharin (0.1 gm) and refluxed under N2 gas for 2 hrs when the solution became clear. The solvent was distilled and the crude was dried under high vacuum, dissolved in dry THF (2 ml) and was added to a solution of 1 - propynyl Zn [made by the treating 0.5 M solution of 1 -propynyl magnesium bromide (7.8 ml) with dry ZnCI2 (0.3 gm] under nitrogen]. Pd (PPh3)4 (0.15 g) was added followed by the addition of catalytic amount of Cul. The mixture was stirred at room temperature for 3 hrs (tic) and quenched with saturated NH4CI solution. The crude was taken in EtOAc (20 ml) and washed with H20. The organic layer was separated and dried over MgS04. The solvent was distilled and the crude was dissolved in 1 ,4-dioxane (4 ml) and TBAF (0.3 ml, 1 M solution in THF) was added followed by the stirring at reflux for 4 hrs. The solvent was distilled and the crude was purified over FCC (Si02, Hexane/EtOAc) to give the title compound (0.145 g, 91 %) as white solid. 1 H-NMR (CDCI3) 7.78 (s, 1 H); 7.46 - 7.44 (m, 2H); 6.41 (bs, 1 H); 2.47 (s, 3H).
 

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