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Chemical Structure| 55218-76-3 Chemical Structure| 55218-76-3

Structure of 55218-76-3

Chemical Structure| 55218-76-3

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Product Details of [ 55218-76-3 ]

CAS No. :55218-76-3
Formula : C12H9NO
M.W : 183.21
SMILES Code : O=CC1=NC=CC(C2=CC=CC=C2)=C1
MDL No. :MFCD14702184

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Application In Synthesis of [ 55218-76-3 ]

* 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 [ 55218-76-3 ]

[ 55218-76-3 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 2591-86-8 ]
  • [ 54151-74-5 ]
  • [ 55218-76-3 ]
YieldReaction ConditionsOperation in experiment
1B. 4-Phenyl-pyridine-2-carbaldehyde: To a clear, colorless solution of lA (0.850 g, 4.5 mmol) in propionitrile (4.5 mmol) was added trimethylsilyl bromide (2.95 mL, 22.4 mmol). The resulting orange suspension was microwaved in a sealed tube at 150 C for 10 min. The reaction was cooled to rt and poured into 1.0 N NaOH containing ice. The aqueous layer was extracted with diethyl ether (2x). The combined organic layers were washed with sat. NaHC03, brine, dried over Na2S04, filtered and concentrated to give 1.07 g of 2-bromo-4-phenyl pyridine as an off-white solid. MS 233.9 (M+H) + and 235.9 (M+2+H)+. [00337] To a cooled (-78 C) clear, slightly yellow solution of 2-bromo-4- phenyl-pyridine (0.500 g, 2.14 mmol) in THF (8.6 mL) was added dropwise 2.5 M n-BuLi in hexane (0.86 mL, 2.14 mmol). The resulting red solution was stirred at-78 C for 1h, then 1-formylpiperidine (0.48 mL, 4.28 mmol) was added dropwise. The reaction was allowed to warm to 0 C over 1h and then stirred at 0 C for 1h. The reaction was quenched with 1.0 N HCl. The reaction was extracted with ethyl acetate. The combined organic layers were washed with sat. NaHC03, brine, dried over Na2S04, filtered, and concentrated to give 0.555 gas a golden oil. Column chromatography (40 g silica gel; gradient elution; 0-40% ethyl acetate/hexane) provided 1B (0.194 g, 49%) as a yellow solid. ¹H-NMR (400 MHz, CDCI3) No.: 10.16 (s, 1H), 8.84 (d, J = 5.3 Hz, 1H), 8.21 (d, J = 1.3 Hz, 1H), 7.75 (dd, J = 5.3, 1.8 Hz, 1H), 7.71-7.69 (m, 2H), 7.55-7.48 (m, 3H). MS 184.1 (M+H)+.
 

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