Triethylamine → 5-[4-(5-Chloropent-1-yn-1-yl)-2-methoxyphenyl]-2-methyl-1,3-oxazole

HRID 71210

Reaktionsgleichung

Reaktionsgleichung von HRID 71210
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][C:11]([CH3:13])=[N:10][CH:9]=2)=[C:4]([O:14][CH3:15])[CH:3]=1.[Cl:16][CH2:17][CH2:18][CH2:19][C:20]#[CH:21].C(N(CC)CC)C>C(OCC)(=O)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>[Cl:16][CH2:17][CH2:18][CH2:19][C:20]#[C:21][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][C:11]([CH3:13])=[N:10][CH:9]=2)=[C:4]([O:14][CH3:15])[CH:3]=1

Komponenten

7

Edukt 3

HCID 8471TriethylamineHCID 843081-Pentyne, 5-chloro-HCID 666087325-(4-Bromo-2-methoxyphenyl)-2-methyloxazole

Produkt 1

HCID 666082675-[4-(5-Chloropent-1-yn-1-yl)-2-methoxyphenyl]-2-methyl-1,3-oxazole

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 178418476HCID 178418476, VerbindungKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

A mixture of 5-(4-bromo-2-methoxyphenyl)-2-methyl-1,3-oxazole (6.00 g), 5-chloropent-1-yne (4.74 mL), dichlorobis(triphenylphosphine)palladium(II) (1.57 g), copper(I) iodide (426 mg) and triethylamine (60 mL) was stirred at 70° C. for 3 hr, and diluted with ethyl acetate, and the mixture was filtered through celite. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (4.85 g).

Aufarbeitung

  1. filtrationthe mixture was filtered through celite
  2. customThe solvent was evaporated under reduced pressure
  3. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-4cc6270886fc4692977c650aa62d336b
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08822699B2

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