1-Butyne → 2-(1-Butynyl)pyridine

HRID 1181855

反応式

HRID 1181855 の反応式
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[CH:8]#[C:9][CH2:10][CH3:11]>C(NCC)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu](I)I>[C:8]([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1)#[C:9][CH2:10][CH3:11]

参加物

6

反応物 2

HCID 78461-ButyneHCID 79732-Bromopyridine

生成物 1

HCID 212993912-(1-Butynyl)pyridine収率 84.3%

試薬・触媒・溶媒 3

HCID 83717Copper iodide触媒HCID 178418476HCID 178418476、化合物触媒HCID 8021Diethylamine溶媒

実験手順

After dissolving 2-bromopyridine (50 g) in diethylamine (500 mL) and adding dichlorobis(triphenylphosphine)palladium (II) (2.2 g) and copper iodide (0.3 g), the mixture was stirred at room temperature for 4 hours while introducing 1-butyne (100 g) as a gas. After bubbling in nitrogen, extraction was performed with ethyl acetate. The insoluble portion was filtered out with celite, and then the organic layer was washed with water and brine. After drying over anhydrous magnesium sulfate and filtration, the solvent was concentrated under reduced pressure, the residue was purified by silica gel column chromatography, and the title compound (35 g) was obtained from the n-hexane:ethyl acetate (5:1) fraction as a brown oil.

後処理

  1. customAfter bubbling in nitrogen
  2. extractionextraction
  3. filtrationThe insoluble portion was filtered out with celite
  4. washthe organic layer was washed with water and brine
  5. dry with materialAfter drying over anhydrous magnesium sulfate and filtration
  6. concentrationthe solvent was concentrated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-457cd82ce59544778e5b01d6a0b20f2d
出典データセット
uspto-grants-2007_10
特許番号
US07285666B2

関連ノート

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