1-Butyne → 2-(1-Butynyl)pyridine

HRID 1864980

반응식

HRID 1864980 반응식
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]

참가 물질

6

반응물 2

HCID 78461-ButyneHCID 79732-Bromopyridine

생성물 1

HCID 212993912-(1-Butynyl)pyridine수율 84.3%

시약·촉매·용매 3

HCID 83717Copper iodide촉매HCID 178418476HCID 178418476, 화합물촉매HCID 8021Diethylamine용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-3820b64e8f904a2488ad297be356a517
출처 데이터셋
uspto-grants-2009_12
특허 번호
US07625925B2

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