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Chemical Structure| 345264-52-0 Chemical Structure| 345264-52-0

Structure of 345264-52-0

Chemical Structure| 345264-52-0

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Product Details of [ 345264-52-0 ]

CAS No. :345264-52-0
Formula : C10H11NO
M.W : 161.20
SMILES Code : OCCC1=CC=CC2=C1NC=C2
MDL No. :MFCD09926293

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Application In Synthesis of [ 345264-52-0 ]

* 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 [ 345264-52-0 ]

[ 345264-52-0 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 408354-47-2 ]
  • [ 15121-84-3 ]
  • [ 345264-52-0 ]
YieldReaction ConditionsOperation in experiment
b) 2-(lH-Indol-7-yl) ethanol; Slowly add a 1.0 molar solution of vinylmagnesium bromide in tetrahydrofuran (430 mL, 430 mmol) to a stirred solution of 2- (2-nitrophenyl)-1- (tert- butyldimethylsilyloxy) ethane (27.4, 97.3 mmol) in anhydrous tetrahydrofuran (300 mL) under nitrogen, maintaining the internal temperature of the reaction between-48°C and- 43°C. Stir at-45°C for 45 minutes. Pour into 1.5 liters of stirring aqueous saturated ammonium chloride and extract with 50percent hexane, 50percent diethyl ether. Dry over anhydrous magnesium sulfate, filter, and concentrate under reduced pressure. Chromatography on flash silica using a gradient from neat hexane to 7percent ethyl acetate in hexane gives 14.4 g of a brown oil, which is a mixture of the tert-butyldimethylsilyl protected product and starting material. Dissolve the brown oil in tetrahydrofuran (500 mL), add distilled water (100 mL), and cool the mixture to 15°C. Add 1M aqueous hydrochloric acid (100 mL), then stir at 15°C for 2 hours. Add solid sodium hydrogen carbonate until the reaction mixture is basic, and saturate by adding solid sodium chloride. Separate, filter, and concentrate under reduced pressure to obtain 9.3 of a brown oil, which is a mixture of the title compound and 2-nitrophenethyl alcohol. Dissolve the brown oil in tetrahydrofuran (100 mL), add absolute ethanol (50mL), then add 10percent palladium on carbon, and stir the mixture under hydrogen (1 atm) at 20°C, for 2 hours. Dilute the mixture with ethyl acetate and filter through a pad of Celite . Wash with 0.2M aqueous hydrochloric acid, aqueous saturated sodium hydrogen carbonate, and saturated sodium chloride. Dry over anhydrous magnesium sulfate, filter, concentrate under reduced pressure. Chromatography on flash silica using ethyl acetate, hexane gives 6.9 g (44percent) of the title compound as an off-white solid. HRMS (M+H) = 162.0924.
 

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