Triethylamine → 2-Methyl-3-((trimethylsilyl)ethynyl)pyridine

HRID 1645619ノート

反応式

HRID 1645619 の反応式
FC(F)(F)S(O[C:7]1[C:8]([CH3:13])=[N:9][CH:10]=[CH:11][CH:12]=1)(=O)=O.[CH3:16][Si:17]([C:20]#[CH:21])([CH3:19])[CH3:18].C(N(CC)CC)C>CN(C)C=O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.[Cu]I>[CH3:13][C:8]1[C:7]([C:21]#[C:20][Si:17]([CH3:19])([CH3:18])[CH3:16])=[CH:12][CH:11]=[CH:10][N:9]=1

参加物

7

反応物 3

HCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 107764652-Methylpyridin-3-yl trifluoromethanesulfonate

生成物 1

HCID 597925602-Methyl-3-((trimethylsilyl)ethynyl)pyridine収率 84.1%

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 6102075Dichlorobis(triphenylphosphine)palladium触媒HCID 6228Dimethylformamide溶媒

実験手順

First, 2-methylpyridin-3-yl trifluoromethanesulfonate (34.3 g, 142 mmol), trimethylsilylacetylene (30 ml, 212 mmol), bis(triphenylphosphine)palladium (II) chloride (10.0 g, 14.2 mmol), and copper (I) iodide (2.75 g, 14.4 mmol) were dissolved in N,N-dimethyl formamide (150 ml). Thereafter, triethylamine (43 ml, 309 mmol) was added in a nitrogen atmosphere at room temperature to the mixture. The mixture was then stirred for 3 hours (exothermic reaction took place). The reaction mixture was separated by ethyl acetate and a saturated aqueous ammonium chloride solution and insoluble substance was removed by filtration. The organic layer of the filtrate was washed twice with a saturated aqueous ammonium chloride solution, dried over anhydrous magnesium sulfate, filtrated and concentrated to obtain the title compound (22.6 g, yield: 84.1%) as brown oil.

後処理

  1. custom(exothermic reaction took place)
  2. customThe reaction mixture was separated by ethyl acetate
  3. customa saturated aqueous ammonium chloride solution and insoluble substance was removed by filtration
  4. washThe organic layer of the filtrate was washed twice with a saturated aqueous ammonium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltrated
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-9cff5c72c9d14062855004377692b469
出典データセット
uspto-grants-2012_02
特許番号
US08124780B2

反応ノート

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