Hydrochloric Acid → 2-Ethynyl-6-methylpyridine

HRID 8214

Reaktionsgleichung

Reaktionsgleichung von HRID 8214
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[N:3]=1.C[Si]([C:13]#[CH:14])(C)C.[OH-].[Na+].Cl>C(N(CC)CC)C.CO.[Cu]I.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>[C:13]([C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[N:3]=1)#[CH:14]

Komponenten

9

Edukt 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 66111TrimethylsilylacetyleneHCID 792052-Bromo-6-methylpyridine

Produkt 1

HCID 134006352-Ethynyl-6-methylpyridineAusbeute 341,4 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 178418476HCID 178418476, VerbindungKatalysatorHCID 887MethanolLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

A solution of 2-bromo-6-methylpyridine (0.5 g, 2.9 mmol) and (trimethylsilyl)acetylene (0.29 g, 2.9 mmol) in triethylamine (15 mL) is purged with argon. Copper(I) iodide (11 mg, 0.06 mmol) and (PPh3)2PdCl2 (42 mg, 0.06 mmol) are added and the reaction is stirred under argon at room temperature for 2 h. The solvent is removed in vacuo and the residue is diluted in ethyl acetate (50 mL) and water (50 mL). The organic is separated and washed with brine. The solvent is removed to afford a dark oil. This oil is diluted in methanol (50 mL) and treated with a 1 N sodium hydroxide solution (10 mL) and stirred for 3 h at room temperature. The aqueous is neutralized with 1 N hydrochloric acid and extracted with ethyl acetate. The solvent is removed in vacuo to afford a dark oil that is purified by SiO2 column chromatography to yield 1.16 g (24%) of the title compound as a light yellow oil.

Aufarbeitung

  1. customThe solvent is removed in vacuo
  2. additionthe residue is diluted in ethyl acetate (50 mL)
  3. customThe organic is separated
  4. washwashed with brine
  5. customThe solvent is removed
  6. customto afford a dark oil
  7. stirringstirred for 3 h at room temperature
  8. extractionextracted with ethyl acetate
  9. customThe solvent is removed in vacuo
  10. customto afford a dark oil that
  11. customis purified by SiO2 column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-24f8476f7c90486db479cc7ee0b431c1
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07087626B2

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