2-Bromopyridine → 5-(Pyridin-2-yl)pent-4-yn-1-ol

HRID 654935Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 654935
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:27]([OH:32])[CH2:28][CH2:29][C:30]#[CH:31].[OH-].[Na+]>C(N(CC)CC)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.[Cu]I>[N:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[C:31]#[C:30][CH2:29][CH2:28][CH2:27][OH:32]

Komponenten

8

Edukt 4

HCID 79732-BromopyridineHCID 11776TriphenylphosphineHCID 14798Sodium HydroxideHCID 793464-Pentyn-1-ol

Produkt 1

HCID 109973535-(Pyridin-2-yl)pent-4-yn-1-ol

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 167845palladium(II) acetateKatalysatorHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

A mixture of 2-bromopyridine (5 g, 31.6 mmol), palladium (II) acetate (5 mg), copper (I) iodide (5 mg), triphenylphosphine (5 mg) in triethylamine (40 ml) was deaerated with argon for 5 minutes. After 4-pentyn-1-ol (3.49 ml, 37.9 mmol) was added, the solution was rapidly heated to reflux under argon and conditions maintained for 22 hours. On cooling, the mixture was poured into 2M sodium hydroxide (ca. 30 ml) and extracted thoroughly with ethyl acetate. Evaporation of the dried (magnesium sulphate) extracts gave an oil, which was flash chromatographed on silica using 60% ethyl acetate/chloroform. Fractions with Rf of about 0.12 on evaporation gave the title alcohol as a pale brown oil.

Aufarbeitung

  1. temperaturethe solution was rapidly heated
  2. temperatureto reflux under argon
  3. temperatureconditions maintained for 22 hours
  4. temperatureOn cooling
  5. extractionextracted thoroughly with ethyl acetate
  6. customEvaporation of the
  7. dry with materialdried (magnesium sulphate)
  8. customextracts gave an oil, which
  9. customchromatographed on silica using 60% ethyl acetate/chloroform
  10. customFractions with Rf of about 0.12 on evaporation

Quellen und Nachweise

ORD-Eintrag
ord-971fc2b89bb14941ab94843120053329
Quelldatensatz
uspto-grants-1992_07
Patentnummer
US05134128

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