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Chemical Structure| 59781-08-7 Chemical Structure| 59781-08-7
Chemical Structure| 59781-08-7

5-(Benzyloxy)picolinaldehyde

CAS No.: 59781-08-7

4.5 *For Research Use Only !

Cat. No.: A101106 Purity: 95%

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Product Details of [ 59781-08-7 ]

CAS No. :59781-08-7
Formula : C13H11NO2
M.W : 213.23
SMILES Code : O=CC1=NC=C(OCC2=CC=CC=C2)C=C1
MDL No. :MFCD10697537

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Application In Synthesis of [ 59781-08-7 ]

* 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 [ 59781-08-7 ]

[ 59781-08-7 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 31191-08-9 ]
  • [ 100-39-0 ]
  • [ 59781-08-7 ]
YieldReaction ConditionsOperation in experiment
1.33 g With potassium carbonate; In acetonitrile; at 85℃;Inert atmosphere; To a solution of Compound 32a (500 mg, 4.06 mmol) in dry acetonitrile (20 mL), BnBr (507 ul, 4.26 mmol) and K2CO3 (674 mg,4.87 mmol) were added under N2 atmosphere in order. Then, the mixture was stirred at 85 C for 10 h. After the reaction was completed, the mixture was quenched with water and extracted with EtOAc. The solvent was removed under reduced pressure to get 1.33 g residue 33a. To a solution of Compound 33a (1.33 g, 6.25 mmol) in dry DMF(40 mL), 1,4-diacetylpiperazine-2,5-dione (3.09 g, 15.61 mmol) was added under N2 atmosphere. Then Cs2CO3 (3.05 g, 9.37 mmol) was added to the solution, and the mixture was stirred at 50 C for 24 h. After the reaction was completed, the mixture was dropped to ice water,and filtered to get 34a without further purification. To a solution of benzaldehyde (320 ul, 3.15 mmol) in dry DMF (30 mL), intermediate 34a (920.8 mg, 2.62 mmol) was added under N2 atmosphere. Then Cs2CO3 (1.28 g, 3.93 mmol) was added into the solution, and the mixture was stirred at 50 C for about 24 h. After the reaction was completed, the mixture was diluted with brine and extracted with EtOAc.The organic layer was washed with brine and was dried over anhydrous sodium sulfate (Na2SO4). Then solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography using CH2Cl2/MeOH (50:1) to give yellow solid Compound 8a (427 mg, 0.16 mmol, 41.0% yield).
 

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