1H-1,2,4-Triazole → 1-[3-[4-[2-[(E)-2-phenylethenyl]-4-oxazolylmethoxy]phenyl]propyl]-1,2,4-triazole

HRID 322341Notes

Reaction equation

HRID 322341 reaction equation
[C:1]1(/[CH:7]=[CH:8]/[C:9]2[O:10][CH:11]=[C:12]([CH2:14][O:15][C:16]3[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][CH2:24]O)=[CH:18][CH:17]=3)[N:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(P(CCCC)CCCC)CCC.[NH:39]1[CH:43]=[N:42][CH:41]=[N:40]1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1.O>[C:1]1(/[CH:7]=[CH:8]/[C:9]2[O:10][CH:11]=[C:12]([CH2:14][O:15][C:16]3[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][CH2:24][N:39]4[CH:43]=[N:42][CH:41]=[N:40]4)=[CH:18][CH:17]=3)[N:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 92571H-1,2,4-TriazoleHCID 13831TributylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 155216713-[4-[2-[(E)-2-phenylethenyl]-4-oxazolylmethoxy]phenyl]propanol

Product 1

HCID 155216721-[3-[4-[2-[(E)-2-phenylethenyl]-4-oxazolylmethoxy]phenyl]propyl]-1,2,4-triazoleYield 70%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-[4-[2-[(E)-2-phenylethenyl]-4-oxazolylmethoxy]phenyl]propanol (760 mg), tributyl phosphine (1.01 g) and 1,2,4-triazole (280 mg) in tetrahydrofuran (15 ml) was added dropwise, at 0° C., diethyl azodicarboxylate (700 mg). The mixture was heated for one hour under reflux, poured into water, and extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried (MgSO4), and concentrated. The residue was subjected to a silica gel column chromatography. The crystals obtained from the fraction eluted with ethyl acetate-hexane (2:1, v/v) were recrystallized from ethyl acetate-hexane to give 1-[3-[4-[2-[(E)-2-phenylethenyl]-4-oxazolylmethoxy]phenyl]propyl]-1,2,4-triazole (540 mg, 70%) as colorless prisms, mp 108-109° C.

Workup

  1. temperatureThe mixture was heated for one hour
  2. temperatureunder reflux
  3. extractionextracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with water
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customThe crystals obtained from the fraction
  8. washeluted with ethyl acetate-hexane (2:1
  9. customv/v) were recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-d45e79e1af26418f93335cb812c26437
Source dataset
uspto-grants-2001_04
Patent number
US06211215B1

Reaction notes

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