Bromide ion → HCID 178435592, Verbindung

HRID 486502Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 486502
[Br-].[CH2:2]([Li])CCC.[PH4+].[CH2:8]([C:12]1[NH:13][C:14]2[C:19]([C:20](=[O:22])[N:21]=1)=[CH:18][C:17]([CH:23]=O)=[CH:16][CH:15]=2)[CH2:9][CH2:10][CH3:11]>O1CCCC1>[CH2:8]([C:12]1[NH:13][C:14]2[C:19]([C:20](=[O:22])[N:21]=1)=[CH:18][C:17]([CH:23]=[CH2:2])=[CH:16][CH:15]=2)[CH2:9][CH2:10][CH3:11]

Komponenten

6

Edukt 4

HCID 259Bromide ionHCID 5460504PhosphoniumHCID 178418339ButyllithiumHCID 178441857HCID 178441857, Verbindung

Produkt 1

HCID 178435592HCID 178435592, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

To a suspension of 15.14 g of mothyltriphenylphosphonium bromide in tetrahydrofuran, cooled to -78° C., is slowly added 21.73 ml of 1.95 M n-butyllithium in hexanes. The reaction mixture is allowed to warm to room temperature and stirred until all of the phosphonium salt dissolves. This takes approximately 30 minutes. The reaction mixture is cooled to -78° C. and 1.95 g of 2-butyl-1,4-dihydro-4-oxo-6-quinazolinecarboxaldehyde added in one portion as a solid. The reaction mixture is allowed to warm to room temperature and stirred for 18 hours. The reaction mixture is quenched with saturated ammonium chloride, diluted with water and extracted with ethyl acetate. The organic layer is separated, washed with briner dried with MgSO4 and concentrated in vacuo to a residue which is purified by chromatography on silica gel using 1:3 ethyl acetate-hexanes to give 2.48 g of the desired product as a solid. CI MASS SPEC 229 (M+H)

Aufarbeitung

  1. temperatureto warm to room temperature
  2. dissolutiondissolves
  3. customThis takes approximately 30 minutes
  4. temperatureThe reaction mixture is cooled to -78° C.
  5. temperatureto warm to room temperature
  6. customThe reaction mixture is quenched with saturated ammonium chloride
  7. additiondiluted with water
  8. extractionextracted with ethyl acetate
  9. customThe organic layer is separated
  10. washwashed with briner
  11. dry with materialdried with MgSO4
  12. concentrationconcentrated in vacuo to a residue which
  13. customis purified by chromatography on silica gel using 1:3 ethyl acetate-hexanes

Quellen und Nachweise

ORD-Eintrag
ord-52b9c5e89abc46a0adec21ba147f37ea
Quelldatensatz
uspto-grants-1994_03
Patentnummer
US05292734

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