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Chemical Structure| 40534-33-6 Chemical Structure| 40534-33-6

Structure of 40534-33-6

Chemical Structure| 40534-33-6

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Product Details of [ 40534-33-6 ]

CAS No. :40534-33-6
Formula : C6H10N2O
M.W : 126.16
SMILES Code : CC(O)C1=CN(C)N=C1
MDL No. :MFCD08700894

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Application In Synthesis of [ 40534-33-6 ]

* 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 [ 40534-33-6 ]

[ 40534-33-6 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 40534-33-6 ]
  • [ 37687-18-6 ]
YieldReaction ConditionsOperation in experiment
91% With manganese(IV) oxide; In dichloromethane; at 0 - 20℃; for 14h; 3) 1-(1-Methyl-1H-pyrazol-4-yl) ethanone In an argon atmosphere and at 0C, manganese(IV) oxide (activated, <5 micron, 209 g) was added to a solution of the above 1-(1-methyl-1H-pyrazol-4-yl)ethanol (20.2 g) in dichloromethane (202 mL), and the mixture was stirred for 14 hours at room temperature. Solid matter in the reaction mixture was removed through filtration, and the solvent of the filtrate was evaporated under reduced pressure, to thereby give 1-(1-methyl-1H-pyrazol-4-yl)ethanone as a solid product (18.1 g, 91%). 1H-NMR(400MHz,CDCl3)delta:2.42(3H,s), 3.94(3H,s), 7.86(1H,s), 7.89(1H,s). ESI-MSm/z:125(M+H)+.
  • 2
  • [ 37687-18-6 ]
  • [ 40534-33-6 ]
YieldReaction ConditionsOperation in experiment
159 mg With sodium tetrahydroborate; In methanol; at 0 - 20℃; 1-(1-Methyl-1H-pyrazol-4-yl)ethan-1-ol. To a resealable vial was added 4-iodo-1-methyl-1H-pyrazole (772 mg, 3.71 mmol), THF (6 mL), and the solution was cooled to 0 C. To this solution was added isopropylmagnesium chloride lithium chloride complex solution (3.42 mL, 4.45 mmol) and the reaction stirred for 30 min (complete disappearance of iodo-pyrazole as detected via LCMS) before cooling to -78 C and addition of N-methoxy-N-methylacetamide (1.18 mL, 11.13 mmol). The solution was stirred at -78 C for 1 h before removing the cold bath and warming to ambient temperature. The solution was diluted with EtOAc and quenched via the addition of 1N HCl. The layers were separated and the aqueous was extracted with EtOAc. The combined organics layer was washed with brine, dried over Na2SO4, filtered, and concentrated. The crude residue was taken up in MeOH and cooled to 0 C before addition of NaBH4 (281 mg, 7.42 mmol). The reaction was stirred while warming to ambient temperature and quenched when LCMS showed disappearance of starting material. This solution was then diluted with 1N HCl and EtOAc. The layers were separated and the aqueous was extracted with EtOAc (3X). The combined organic layer was washed with brine, dried over Na2SO4, filtered, and concentrated. The crude material was purified via silica gel chromatography (MeOH:DCM) to afford 1-(1-methyl-1H-pyrazol-4-yl)ethanol (159 mg, 1.260 mmol, 34.0 % yield). LC-MS m/z 127 [M + H]+.
 

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