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Chemical Structure| 1249610-72-7 Chemical Structure| 1249610-72-7

Structure of 1249610-72-7

Chemical Structure| 1249610-72-7

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Product Details of [ 1249610-72-7 ]

CAS No. :1249610-72-7
Formula : C7H8ClNO
M.W : 157.60
SMILES Code : COCC1=CC(Cl)=NC=C1
English Name :2-Chloro-4-(methoxymethyl)pyridine
MDL No. :MFCD16765210

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Application In Synthesis of [ 1249610-72-7 ]

* 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 [ 1249610-72-7 ]

[ 1249610-72-7 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 100704-10-7 ]
  • [ 74-88-4 ]
  • [ 1249610-72-7 ]
YieldReaction ConditionsOperation in experiment
73% With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; Intermediate 136: 2-chloro-4-(methoxymethyl)pyridine To a solution of (2-chloro-4-pyridyl)methanol (830 mg, 5.78 mmol) in 17 mL of anh. DMF was added at 0 °C NaH (60 %, 243 mg, 6.07 mmol) followed by the addition of methyl iodide (486 μL, 7.80 mmol) dropwise. The mixture was left stirring at 0 °C. By HPLC-MS is observed that the reaction does not progress once achieved 80 % of conversion. NH4C1 sat. was added (at 0 °C) and the solution extracted twice with AcOEt. The organic fractions were washed with water (x 2), LiCl (5 % aq., x 2) and brine; dried over anh. MgS04, filtered and evaporated to have an orange oil which was purified by flash chromatography in Hx/Hx with 50 % Et20 to have a colorless oil (663 mg, 73 %). HPLC-MS: tr = 2.17 min. (99 %). LRMs (m/z): 158/160 (M+l, 1 Cl) lH NMR 1H (CDC13, 400 MHz) d ppm 3.44 (s 3H), 4.46 (s 2H), 7.16 (d J=5 Hz 1H), 7.31 (s 1H), 8.33 (d J=5 Hz 1H).
With sodium hydride In tetrahydrofuran; mineral oil Cooling with ice; 27.ii To an ice-cold solution of Compound II (850 mg) in tetrahydrofuran (10 mL) were added sodium hydride (517 mg) and methyl iodide (0.74 mL), and the mixture was stirred overnight. The reaction mixture was diluted with brine, extracted with ethyl acetate, dehydrated with sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=4/1) to give Compound III (674 mg).
 

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