3,5-Dimethylisoxazole → 5-[2-(4-Bromomethylcyclohexyl)ethyl]-3-methylisoxazole

HRID 359843

Reaktionsgleichung

Reaktionsgleichung von HRID 359843
C([Li])CCC.[CH3:6][C:7]1[CH:11]=[C:10]([CH3:12])[O:9][N:8]=1.[Br:13][CH2:14][CH:15]1[CH2:20][CH2:19][CH:18]([CH2:21]Br)[CH2:17][CH2:16]1>O1CCCC1>[Br:13][CH2:14][CH:15]1[CH2:20][CH2:19][CH:18]([CH2:21][CH2:12][C:10]2[O:9][N:8]=[C:7]([CH3:6])[CH:11]=2)[CH2:17][CH2:16]1

Komponenten

5

Edukt 3

HCID 93123,5-DimethylisoxazoleHCID 36135451,4-Bis(bromomethyl)cyclohexaneHCID 178418339Butyllithium

Produkt 1

HCID 200641045-[2-(4-Bromomethylcyclohexyl)ethyl]-3-methylisoxazoleAusbeute 58 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Butyllithium (23.3 ml, 8.0M in tetrahydrofuran) was added dropwise to a solution of 18.3 g of 3,5-dimethylisoxazole in 800 ml of tetrahydrofuran held at -77° C. under nitrogen, and the mixture was stirred for 30 minutes. 1,4-bis(Bromomethyl)cyclohexane (50.4 g) was then added, and the reaction mixture was stirred for 3 hours at -70° C. and at room temperature overnight. The product was isolated and purified by chromatography to give 31 g (58%) of 5-[2-(4-bromomethylcyclohexyl)ethyl]-3-methylisoxazole as a liquid used directly in the next reaction.

Aufarbeitung

  1. customheld at -77° C. under nitrogen
  2. stirringthe reaction mixture was stirred for 3 hours at -70° C. and at room temperature overnight
  3. customThe product was isolated
  4. custompurified by chromatography

Quellen und Nachweise

ORD-Eintrag
ord-50841d247d3d4b39b0a8db65777996b8
Quelldatensatz
uspto-grants-1991_03
Patentnummer
US05002960

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