Ammonium Chloride → (3-(4-Benzyloxy-phenyl)-prop-1-ynyl)-trimethylsilane

HRID 77857

反応式

HRID 77857 の反応式
[CH3:1][Si:2]([C:5]#[CH:6])([CH3:4])[CH3:3].C([Mg]Br)C.[CH2:11]([O:18][C:19]1[CH:26]=[CH:25][C:22]([CH2:23]Cl)=[CH:21][CH:20]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[Cl-].[NH4+]>O1CCCC1.[Cu]Br>[CH2:11]([O:18][C:19]1[CH:20]=[CH:21][C:22]([CH2:23][C:6]#[C:5][Si:2]([CH3:4])([CH3:3])[CH3:1])=[CH:25][CH:26]=1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

参加物

7

反応物 4

HCID 25517Ammonium ChlorideHCID 66111TrimethylsilylacetyleneHCID 700424-Benzyloxybenzyl chlorideHCID 178418443HCID 178418443、化合物

生成物 1

HCID 42642731(3-(4-Benzyloxy-phenyl)-prop-1-ynyl)-trimethylsilane収率 72%

試薬・触媒・溶媒 2

HCID 24593copper(I) bromide触媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
65 °C

実験手順

To a solution of trimethylsilyl acetylene (851 μL, 6.02 mmol) in tetrahydrofuran (20 mL) was added ethyl magnesium bromide (3 M diethyl ether solution, 1.86 mL, 5.59 mmol) under nitrogen atmosphere at room temperature, which was stirred for 40 minutes at 65° C. The reaction solution was cooled to room temperature, and copper (I) bromide (308 mg, 2.16 mmol) and 4-benzyloxybenzyl chloride (1.00 g, 4.30 mmol) were added to the reaction solution and stirred for 8 hours and 45 minutes at 65° C. Saturated ammonium chloride solution was added to the reaction solution at room temperature, which was then extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride and dried over anhydrous magnesium sulfate, and the solvent was evaporated under a reduced pressure. The residue was purified by NH silica gel column chromatography (heptane:ethyl acetate=30:1) to obtain the title compound (911 mg, 72%).

後処理

  1. temperatureThe reaction solution was cooled to room temperature
  2. stirringstirred for 8 hours and 45 minutes at 65° C
  3. extractionwhich was then extracted with ethyl acetate
  4. washThe organic layer was washed with saturated aqueous sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under a reduced pressure
  7. customThe residue was purified by NH silica gel column chromatography (heptane:ethyl acetate=30:1)

出典と根拠

ORDレコード
ord-7cec689e16cf43e5950b9715356415a2
出典データセット
uspto-grants-2014_09
特許番号
US08841327B2

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