3-Methylbut-1-yne → HCID 69959296, Verbindung

HRID 369736Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 369736
[CH:1]([C:4]#[CH:5])([CH3:3])[CH3:2].C([Li])CCC.[NH2:11][C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:13]=1[C:19](=[O:24])[C:20]([F:23])([F:22])[F:21]>C1COCC1>[NH2:11][C:12]1[C:13]([C:19]([OH:24])([C:5]#[C:4][CH:1]([CH3:3])[CH3:2])[C:20]([F:23])([F:21])[F:22])=[CH:14][C:15]([F:18])=[CH:16][CH:17]=1

Komponenten

5

Edukt 3

HCID 690193-Methylbut-1-yneHCID 120519091-(2-Amino-5-fluorophenyl)-2,2,2-trifluoroethanoneHCID 178418339Butyllithium

Produkt 1

HCID 69959296HCID 69959296, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To an ice-cooled solution of 1.89 mL of isopropylacetylene in 35 mL of dry THF was added dropwise over 5 min, 10.0 mL of 1.6 M n-butyllithium. The reaction mixture was stirred at 0° for 30 min after which time 828 mg of 1-(2-amino-5-fluorophenyl)-2,2,2-trifluoroethanone was added. The reaction mixture was stirred at 0° for 1.25 h after which time it was quenched with saturated aqueous ammonium chloride and poured onto water. This mixture was extracted twice with ether and the combined extracts were washed with brine dried and evaporated. The residue was purified by column chromatography on silica gel (elution wth ethyl acetate/hexanes) affording 220 mg of the title compound as a tan solid.

Aufarbeitung

  1. additionwas added dropwise over 5 min
  2. additionwas added
  3. customwas quenched with saturated aqueous ammonium chloride
  4. additionpoured onto water
  5. extractionThis mixture was extracted twice with ether
  6. washthe combined extracts were washed with brine
  7. customdried
  8. customevaporated
  9. customThe residue was purified by column chromatography on silica gel (elution wth ethyl acetate/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-eeeadb39e1354d3987e5d0b6d5c259d0
Quelldatensatz
uspto-grants-2000_10
Patentnummer
US06140320

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