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

HRID 322253Notes

Reaction equation

HRID 322253 reaction equation
[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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-1a0c19a7a4b64cb88b3dfd22f4d5a8c4
Source dataset
uspto-grants-2001_04
Patent number
US06211215B1

Reaction notes

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