1-丁炔 → 2-(1-Butynyl)pyridine

HRID 347824

反应方程式

HRID 347824 反应方程式
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]

参与物

6

反应物 2

HCID 78461-丁炔HCID 79732-溴吡啶

产物 1

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

试剂、催化剂与溶剂 3

HCID 83717碘化铜催化剂HCID 178418476HCID 178418476，化合物催化剂HCID 8021二乙胺溶剂

实验过程

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.

后处理

  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

来源与证据

ORD记录
ord-69f16a9920ca41a6859e112a102f60bb
来源数据集
uspto-grants-2007_02
专利号
US07176216B2

关联笔记

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