Sodium Chloride → t-Butyl 5-methylpyrazine-2-carboxylate

HRID 217980

Reaktionsgleichung

Reaktionsgleichung von HRID 217980
[CH3:1][C:2]1[CH:7]=[N:6][C:5]([C:8]([OH:10])=[O:9])=[CH:4][N:3]=1.ClC(Cl)(Cl)C(=N)O[C:15]([CH3:18])([CH3:17])[CH3:16].[Cl-].[Na+].C(OCC)(=O)C>O1CCCC1>[CH3:1][C:2]1[N:3]=[CH:4][C:5]([C:8]([O:10][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:9])=[N:6][CH:7]=1

Komponenten

6

Edukt 4

HCID 5234Sodium ChlorideHCID 8857Ethyl AcetateHCID 1228315-Methyl-2-pyrazinecarboxylic acidHCID 2734700Tert-butyl 2,2,2-trichloroethanimidate

Produkt 1

HCID 57475683t-Butyl 5-methylpyrazine-2-carboxylateAusbeute 99,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A boron trifluoride-diethyl ether complex (91.7 IL) was added dropwise to a suspension of 2-methylpyrazine-5-carboxylic acid (1 g) and tert-butyl 2,2,2-trichloroacetimidate (4.75 g) in tetrahydrofuran (20 mL) under ice-cooling. The reaction solution was heated to room temperature and stirred for two hours. A saturated sodium chloride solution and ethyl acetate were added to the reaction solution, and the organic layer was separated. The organic layer was dried over anhydrous magnesium sulfate, and the insoluble matter was separated by filtration. The filtrate was concentrated and purified by silica gel column chromatography to obtain the title compound (1.4 g).

Aufarbeitung

  1. temperaturecooling
  2. customthe organic layer was separated
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. customthe insoluble matter was separated by filtration
  5. concentrationThe filtrate was concentrated
  6. custompurified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-3d4a8bbab8b34cfeb18c9f53f4f1db4b
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08198269B2

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