Hydrochloric Acid → 2-(3,4-Methylenedioxybenzy)pyrazine

HRID 584210

Reaktionsgleichung

Reaktionsgleichung von HRID 584210
Cl[C:2]1[CH:7]=[N:6][CH:5]=[CH:4][N:3]=1.[CH2:8]1[O:19][C:18]2[CH:17]=[CH:16][C:12]([CH2:13][Mg]Cl)=[CH:11][C:10]=2[O:9]1.Cl>O1CCCC1.C1C=CC(P(C2C=CC=CC=2)CCP(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Ni]Cl>[CH2:8]1[O:19][C:18]2[CH:17]=[CH:16][C:12]([CH2:13][C:2]3[CH:7]=[N:6][CH:5]=[CH:4][N:3]=3)=[CH:11][C:10]=2[O:9]1

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 73277ChloropyrazineHCID 178478992HCID 178478992, Verbindung

Produkt 1

HCID 223428382-(3,4-Methylenedioxybenzy)pyrazine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 2734542[1,2-Bis(diphenylphosphino)ethane]dichloronickel(II)KatalysatorHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
5 °C

Versuchsvorschrift

To a stirred solution of chloropyrazine (1.14 g) and [1,2-bis(diphenylphosphino)ethane]nickel(II) chloride (106 mg) in dry tetrahydrofuran (40 ml) was added a solution of 3,4-methylenedioxybenzylmagnesium chloride (0.6 M in tetrahydrofuran, 29 ml) at 5° C. under nitrogen atmosphere over 15 minutes. After 1 hour of stirring at 5° C., 3N hydrochloric acid was added slowly under nitrogen atmosphere and the mixture was stirred for 1 hour. The organic layer was separated and the aqueous layer was extracted with ethyl acetate. The combined extract was washed with water and dried over magnesium sulfate. The usual work up followed by flash chromatography on silica gel with a mixture of n-hexane and ethyl acetate (10:1-4:1) gave 2-(3,4-methylenedioxybenzyl)pyrazine (454 mg) as a colorless oil.

Aufarbeitung

  1. stirringthe mixture was stirred for 1 hour
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with ethyl acetate
  4. extractionThe combined extract
  5. washwas washed with water
  6. dry with materialdried over magnesium sulfate
  7. additionThe usual work up followed by flash chromatography on silica gel with a mixture of n-hexane and ethyl acetate (10:1-4:1)

Quellen und Nachweise

ORD-Eintrag
ord-20913b05998346c2b80e48de993a9b99
Quelldatensatz
uspto-grants-2005_08
Patentnummer
US06924278B2

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