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Chemical Structure| 432554-92-2 Chemical Structure| 432554-92-2

Structure of 432554-92-2

Chemical Structure| 432554-92-2

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Product Details of [ 432554-92-2 ]

CAS No. :432554-92-2
Formula : C8H9NO
M.W : 135.16
SMILES Code : OCC1=CC=C(C=C)N=C1
MDL No. :MFCD18819111

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Application In Synthesis of [ 432554-92-2 ]

* 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 [ 432554-92-2 ]

[ 432554-92-2 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 21543-49-7 ]
  • potassium vinyltrifluoroborate [ No CAS ]
  • [ 432554-92-2 ]
YieldReaction ConditionsOperation in experiment
53% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine; In isopropyl alcohol; at 80℃; for 12h;Inert atmosphere; Sealed tube; General procedure: A 100 mL sealed tube was charged with a solution of (6-chloropyridin-3-yl)methanol (0.5 g, 3.4 mmol, Org. Lett. 2005, p 2965-2967) dissolved in isopropanol (10 mL), potassium vinyltrifluoroborate (1 g, 7.63 mmol, Aldrich), [1,1,-bis(diphenyl phosphino)ferrocine]dichloro palladium(II) complex with DCM (0.277 g, 0.34 mmol, Aldrich) and TEA (0.92 mL, 6.8 mmol). The mixture was degassed with nitrogen then heated at about 80 C. for about 12 h. The reaction mixture was cooled to RT, filtered and washed with isopropanol (10 mL). The filtrate was evaporated to dryness under reduced pressure and the crude material obtained was purified by silica gel column chromatography using 30 to 40% of EtOAc in hexane as an eluent. Relevant fractions containing the target compound were combined and evaporated to dryness under reduced pressure to afford (6-vinylpyridin-3-yl)methanol as a dark brown liquid 0.25 g (53%), 1H NMR (400 MHz, DMSO): δ 8.479 (s, 1H), 7.704-7.688 (d, J=6.4 Hz, 1H), 7.471-7.456 (d, J=6.0 Hz, 1H), 6.827-6.806 (m, 1H), 6.212-6.177 (d, J=14 Hz, 1H), 5.439-5.417 (d, J=8.8 Hz, 1H), 5.300 (m, 1H), 4.524 (d, J=4.4 Hz, 2H), MS m/z: 136 (M+H)+.
 

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