4-Bromopyridine → 8-(4-Pyridinyl)-1,4-dioxaspiro[4.5]decan-8-ol

HRID 231215Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 231215
C([Li])CCC.Br[C:7]1[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=1.[CH2:13]1[O:23][C:16]2([CH2:21][CH2:20][C:19](=[O:22])[CH2:18][CH2:17]2)[O:15][CH2:14]1.[Cl-].[NH4+]>CCCCCC.CCOCC.O1CCCC1>[CH2:14]1[O:15][C:16]2([CH2:21][CH2:20][C:19]([OH:22])([C:7]3[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=3)[CH2:18][CH2:17]2)[O:23][CH2:13]1

Komponenten

8

Edukt 4

HCID 142684-BromopyridineHCID 25517Ammonium ChlorideHCID 5674151,4-Dioxaspiro[4.5]decan-8-oneHCID 178418339Butyllithium

Produkt 1

HCID 137720538-(4-Pyridinyl)-1,4-dioxaspiro[4.5]decan-8-olAusbeute 67,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 3283Diethyl EtherLösungsmittel2×HCID 8028TetrahydrofuranLösungsmittelHCID 8058HexaneLösungsmittel

Versuchsvorschrift

Thirty-five ml of ether was cooled to -78° C., to which 20 ml of a 1.6 mol n-butyl lithium solution in hexane was added. Next, 5 g of 4-bromopyridine was dissolved in 30 ml of ether and the solution was added to the mixture. Then, a solution of 5 g of 1,4-cyclohexanedione monoethyleneacetal in 30 ml of tetrahydrofuran was added to the mixture. After completion of the reaction, the reaction solution was poured into saturated ammonium chloride aqueous solution. The mixture was extracted with chloroform and the extract was purified to give 5 g of 4-hydroxy-4-(4-pyridyl)cyclohexanone ethyleneacetal.

Aufarbeitung

  1. additionwas added
  2. additionthe solution was added to the mixture
  3. customAfter completion of the reaction
  4. extractionThe mixture was extracted with chloroform
  5. customthe extract was purified

Quellen und Nachweise

ORD-Eintrag
ord-424fabbef7374f15a0447ba7747e7663
Quelldatensatz
uspto-grants-1989_07
Patentnummer
US04845228

Notizen zur Reaktion

Wird geladen…