Acetone → HCID 58674658, Verbindung

HRID 1994118Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1994118
Br[C:2]1[CH:3]=[C:4]([N:8]2[C:12]([CH3:13])=[CH:11][CH:10]=[C:9]2[CH3:14])[CH:5]=[CH:6][CH:7]=1.[Li]CCCC.[CH3:20][C:21]([CH3:23])=[O:22]>C1COCC1>[CH3:14][C:9]1[N:8]([C:4]2[CH:3]=[C:2]([C:21]([OH:22])([CH3:23])[CH3:20])[CH:7]=[CH:6][CH:5]=2)[C:12]([CH3:13])=[CH:11][CH:10]=1

Komponenten

5

Edukt 3

HCID 180AcetoneHCID 47636541-(3-bromophenyl)-2,5-dimethyl-1H-pyrroleHCID 178418339Butyllithium

Produkt 1

HCID 58674658HCID 58674658, VerbindungAusbeute 61,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 1-(3-bromophenyl)-2,5-dimethyl-1H-pyrrole (1.50 g, 6.00 mmol) in THF (25 mL) was cooled to −78° C. under an atmosphere of argon. To this solution was added n-BuLi (2.50 M in hexane, 2.76 mL, 6.90 mmol) dropwise via syringe. After 30 min, acetone (0.572 mL, 7.8 mmol) was added to the cold solution dropwise via syringe. After 10 min, the cold bath was removed and the reaction mixture was allowed to warm to rt. After 5.5 h, the reaction was quenched by the addition of water. The mixture was extracted with EtOAc and the organic solutions dried over Na2SO4, filtered, and concentrated. The residue was purified by column chromatography to give the desired product (0.84 g, 61%). LCMS: (FA) ES+ 230.1 (M+1).

Aufarbeitung

  1. waitAfter 10 min
  2. customthe cold bath was removed
  3. waitAfter 5.5 h
  4. customthe reaction was quenched by the addition of water
  5. extractionThe mixture was extracted with EtOAc
  6. dry with materialthe organic solutions dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-8bd329db5afa40d19095c0ad02d41faf
Quelldatensatz
uspto-grants-2010_01
Patentnummer
US07652041B2

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