Triethylamine → 6-(1-Undecynyl)pyridine-2-carboxaldehyde

HRID 743782

반응식

HRID 743782 반응식
Br[C:2]1[N:7]=[C:6]([CH:8]=[O:9])[CH:5]=[CH:4][CH:3]=1.[CH:10]#[C:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20].C(N(CC)CC)C>O1CCCC1.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>[C:10]([C:2]1[N:7]=[C:6]([CH:8]=[O:9])[CH:5]=[CH:4][CH:3]=1)#[C:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]

참가 물질

7

반응물 3

HCID 8471TriethylamineHCID 752491-UndecyneHCID 27570096-Bromopyridine-2-carbaldehyde

생성물 1

HCID 153806466-(1-Undecynyl)pyridine-2-carboxaldehyde수율 84.3%

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 6102075Dichlorobis(triphenylphosphine)palladium촉매HCID 8028Tetrahydrofuran용매

실험 절차

A solution of 6-bromopyridine-2-carboxaldehyde (15.0 g), 1-undecyne (12.9 g), triethylamine (24.5 g), bis(triphenylphosphine)palladium(II)chloride (1.1 g, 2%), and copper(I)iodide (0.15 g, 1%) in dry tetrahydrofuran (60 ml) was heated under nitrogen at 55° C. for 10 hrs. The reaction mixture was filtered, the filter cake was washed with ethyl acetate, and the filtrate was evaporated. The residue was dissolved in ethyl acetate, and the solution was washed with half-saturated sodium chloride solution, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated. The residue was flash chromatographed on silica gel, cluting with 0%-2%-ethyl acetate:hexane. The appropriate fractions were collected and evaporated to yield 17.5 g (84.0%) of product.

후처리

  1. filtrationThe reaction mixture was filtered
  2. washthe filter cake was washed with ethyl acetate
  3. customthe filtrate was evaporated
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washthe solution was washed with half-saturated sodium chloride solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationthe filtrate was concentrated
  9. customchromatographed on silica gel
  10. customThe appropriate fractions were collected
  11. customevaporated

출처 및 근거

ORD 기록
ord-3918e9f1c73e4d41820bfbada4ff9e0e
출처 데이터셋
uspto-grants-1996_09
특허 번호
US05557006

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