Dimethylformamide → (2,4-Difluoro-3-formyl-phenyl)-carbamic acid tert-butyl ester

HRID 1098492Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1098492
[C:1]([O:5][C:6](=[O:16])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([F:14])=[CH:10][C:9]=1[F:15])([CH3:4])([CH3:3])[CH3:2].C([Li])CCC.C([N-]C(C)C)(C)C.[Li+].CN(C)[CH:32]=[O:33]>O1CCCC1>[C:1]([O:5][C:6](=[O:16])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([F:14])=[C:10]([CH:32]=[O:33])[C:9]=1[F:15])([CH3:4])([CH3:2])[CH3:3]

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 2724682Lithium diisopropylamideHCID 22986665Tert-butyl (2,4-difluorophenyl)carbamateHCID 178418339Butyllithium

Produkt 1

HCID 58086596(2,4-Difluoro-3-formyl-phenyl)-carbamic acid tert-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To 2,4-difluoro-phenyl)-carbamic acid tert-butyl ester (123, 1.41 g, 6.17 mmol) in tetrahydrofuran (60.0 mL) under an atmosphere of nitrogen at 78° C. were added n-butyllithium (2.50 M in hexane, 2.59 mL) for 30 min. Lithium diisopropylamide (2.0 M in hexane, 3.4 mL) was added to the reaction. After 35 min, N,N-dimethylformamide (1.05 mL, 0.0136 mol) was added to the reaction mixture. The reaction was allowed to cool to room temperature overnight. The organic layer was washed with brine, dried over sodium sulfate, concentrated and purified by silica gel chromatography, eluting with 20% ethyl acetate in hexane to provide compound 124.

Aufarbeitung

  1. washThe organic layer was washed with brine
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated
  4. custompurified by silica gel chromatography
  5. washeluting with 20% ethyl acetate in hexane

Quellen und Nachweise

ORD-Eintrag
ord-53a6f14eb14448bd8086abcf60cf05e8
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08143271B2

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