Dimethylformamide → 3-(tert-Butoxy)pyrazine-2-carbaldehyde

HRID 606146Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 606146
CC1(C)CCCC(C)(C)N1.C([Li])CCC.[C:16]([O:20][C:21]1[CH:26]=[N:25][CH:24]=[CH:23][N:22]=1)([CH3:19])([CH3:18])[CH3:17].CN(C)[CH:29]=[O:30]>O1CCCC1.C(OCC)(=O)C.O>[C:16]([O:20][C:21]1[C:26]([CH:29]=[O:30])=[N:25][CH:24]=[CH:23][N:22]=1)([CH3:19])([CH3:17])[CH3:18]

Komponenten

8

Edukt 4

HCID 6228DimethylformamideHCID 130352,2,6,6-TetramethylpiperidineHCID 132568902-Tert-butoxypyrazineHCID 178418339Butyllithium

Produkt 1

HCID 222482803-(tert-Butoxy)pyrazine-2-carbaldehydeAusbeute 45 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
-50 °C

Versuchsvorschrift

After dissolving 2.50 ml of 2,2,6,6-tetramethylpiperidine in 40 ml of tetrahydrofuran, the solution was cooled to −50° C. Next, 5.25 ml of n-butyllithium (2.6 M, n-hexane solution) was added dropwise thereto under a nitrogen atmosphere. The mixture was stirred for 25 minutes, cooled on ice, and stirred for an additional 35 minutes. It was then cooled to −78° C., and a solution of 1.89 g of 2-tert-butoxypyrazine [CAS No. 70090-30-1] in tetrahydrofuran (5 ml) was added dropwise. After stirring the mixture for 15 minutes, 1.25 ml of N, N-dimethylformamide was added dropwise. After 10 minutes, water was added to the reaction solution and extraction was performed with ethyl acetate. The organic layer was washed with water and saturated brine in that order and dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (solvent: n-hexane/ethyl acetate) to obtain the title compound (1.00 g, 45% yield).

Aufarbeitung

  1. temperaturecooled on ice
  2. stirringstirred for an additional 35 minutes
  3. temperatureIt was then cooled to −78° C.
  4. stirringAfter stirring the mixture for 15 minutes
  5. waitAfter 10 minutes
  6. washThe organic layer was washed with water and saturated brine in that order
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationthe solvent was distilled off under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (solvent: n-hexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-6f9c7626f9364981953cf2d2a49ab8fc
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07915274B2

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