Dimethylformamide → HCID 18793049, Verbindung

HRID 850647

Reaktionsgleichung

Reaktionsgleichung von HRID 850647
[Li+].CC([N-]C(C)C)C.[Br:9][C:10]1[C:14]([CH2:15][CH2:16][CH2:17][CH3:18])=[CH:13][S:12][CH:11]=1.CN([CH:22]=[O:23])C>C1COCC1>[Br:9][C:10]1[C:14]([CH2:15][CH2:16][CH2:17][CH3:18])=[CH:13][S:12][C:11]=1[CH:22]=[O:23]

Komponenten

5

Edukt 3

HCID 6228DimethylformamideHCID 2724682Lithium diisopropylamideHCID 125026793-Bromo-4-butylthiophene

Produkt 1

HCID 18793049HCID 18793049, VerbindungAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel3×

Versuchsvorschrift

To a solution of freshly prepared LDA (11.40 mmol) in THF (7 mL) at -78° C. was added slowly 3-bromo-4-butylthiophene of Example l(a) (2.50 g, 11.40 mmol) in THF (10 mL). After stirring for 15 min, DMF (0.94 mL, 12.10 mmol) in THF (2 mL) was dropwise added. The resulting mixture was stirred for 1 h at -78° C. and then allowed to warm to room temperature. The reaction was quenched with water and extracted with EtOAc (2×50 mL). The combined organic extracts were washed with H2O, brine and dried (MgSO4). After removing the solvent under reduced pressure, column chromatography (silica gel, EtOAc/Hexane, 20:80) of the residue afforded the title compound as an oil (1.87 g, 60%).

Aufarbeitung

  1. stirringThe resulting mixture was stirred for 1 h at -78° C.
  2. customThe reaction was quenched with water
  3. extractionextracted with EtOAc (2×50 mL)
  4. washThe combined organic extracts were washed with H2O, brine
  5. dry with materialdried (MgSO4)
  6. customAfter removing the solvent under reduced pressure, column chromatography (silica gel, EtOAc/Hexane, 20:80) of the residue

Quellen und Nachweise

ORD-Eintrag
ord-5603aa86c7d14cf6aea3b963e8eb3b67
Quelldatensatz
uspto-grants-2000_01
Patentnummer
US06017952

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