1H-1,2,4-Triazole → 1-[4-(4-Benzyloxyphenyl)butyl]-1,2,4-triazole

HRID 322253Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 322253
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH2:17][CH2:18]O)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(P(CCCC)CCCC)CCC.[NH:33]1[CH:37]=[N:36][CH:35]=[N:34]1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1.O>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH2:17][CH2:18][N:33]2[CH:37]=[N:36][CH:35]=[N:34]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

7

Edukt 4

HCID 92571H-1,2,4-TriazoleHCID 13831TributylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 153287654-(Phenylmethoxy)benzenebutanol

Produkt 1

HCID 220098341-[4-(4-Benzyloxyphenyl)butyl]-1,2,4-triazoleAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 4-(4-benzyloxyphenyl)butanol (3.55 g), tributyl phosphine (6.84 g) and 1,2,4-triazole (1.86 g) in tetrahydrofuran (75 ml) was added dropwise, at room temperature, diethyl azodicarboxylate (40% toluene solution, 11.8 g). The mixture was heated for two hours under reflux. The reaction mixture was poured into water and extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried (MgSO4), and concentrated under reduced pressure. The residue was subjected to a silica gel column chromatography. From the fraction eluted with ethyl acetate-hexane (1:2, v/v), 1-[4-(4-benzyloxyphenyl)butyl]-1,2,4-triazole (3.45 g, 83%) was obtained. Recrystallization from isopropyl ether gave colorless prisms, mp 68-69° C.

Aufarbeitung

  1. temperatureThe mixture was heated for two hours
  2. temperatureunder reflux
  3. extractionextracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with water
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated under reduced pressure
  7. washFrom the fraction eluted with ethyl acetate-hexane (1:2

Quellen und Nachweise

ORD-Eintrag
ord-1a0c19a7a4b64cb88b3dfd22f4d5a8c4
Quelldatensatz
uspto-grants-2001_04
Patentnummer
US06211215B1

Notizen zur Reaktion

Wird geladen…