1-Butyne → 2-(1-Butynyl)pyridine

HRID 347824

反応式

HRID 347824 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

To a solution of 2-bromopyridine (50 g) dissolved in diethylamine (500 mL) was added dichlorobis(triphenylphosphine)palladium(II) (2.2 g) and copper iodide (0.3 g), and the reaction mixture was stirred for 4 hours at room temperature while introducing 1-butyne (100 g) as a gas. The resulting reaction mixture was bubbled with nitrogen, and then ethyl acetate was added. After the reaction mixture was filtered through celite to remove insoluble residue, the filtrate was washed with water and brine. The obtained organic extract was dried over anhydrous magnesium sulfate and filtered, the solvent was evaporated under reduced pressure, the residue was purified by silica gel column chromatography and the title compound (35 g) was obtained as a brown oil from the n-hexane:ethyl acetate (5:1) fraction.

後処理

  1. customThe resulting reaction mixture
  2. customwas bubbled with nitrogen
  3. additionethyl acetate was added
  4. filtrationAfter the reaction mixture was filtered through celite
  5. customto remove insoluble residue
  6. washthe filtrate was washed with water and brine
  7. extractionThe obtained organic extract
  8. dry with materialwas dried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. customthe solvent was evaporated under reduced pressure
  11. customthe residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-69f16a9920ca41a6859e112a102f60bb
出典データセット
uspto-grants-2007_02
特許番号
US07176216B2

関連ノート

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