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

HRID 977540Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 977540
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]

Komponenten

7

Edukt 3

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

Produkt 1

HCID 153806466-(1-Undecynyl)pyridine-2-carboxaldehydeAusbeute 84,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 6102075Dichlorobis(triphenylphosphine)palladiumKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 6-bromopyridine-2-caboxaldehyde (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 (0.15g, 1%) in dry tetrahydrofuran (60 ml) was heated under nitorgen 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, eluting with 0%-2%-ethyl acetate:hexane. The appropriate fractions were collected and evaporated to yield 17.5 g (84.0%) of product.

Aufarbeitung

  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. washeluting with 0%-2%-ethyl acetate
  11. customThe appropriate fractions were collected
  12. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-e918484e906440249990daf664e26c8e
Quelldatensatz
uspto-grants-1997_03
Patentnummer
US05614631

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