tert-Butyl hydroperoxide → HCID 22152403, compound

HRID 1111381Notes

Reaction equation

HRID 1111381 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([OH:24])([C:15]([C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)=[CH2:16])[CH2:9][N:10]2[CH:14]=[N:13][CH:12]=[N:11]2)=[CH:4][CH:3]=1.C([O:29]O)(C)(C)C>C1C=CC=CC=1.[V]>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([OH:24])([C:15]2([C:17]3[CH:18]=[CH:19][C:20]([F:23])=[CH:21][CH:22]=3)[O:29][CH2:16]2)[CH2:9][N:10]2[CH:14]=[N:13][CH:12]=[N:11]2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 6410tert-Butyl hydroperoxideHCID 19913071HCID 19913071, compound

Product 1

HCID 22152403HCID 22152403, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 23990VanadiumCatalystHCID 241BenzeneSolvent

Procedure

2,3-Bis(4-fluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-3-butene-2-ol (1.0 g) was dissolved in 50 ml of anhydrous benzene and stirred under nitrogen. To this solution was added 0.012 g of vanadium acetonylacetonate. The solution was then refluxed and tert-butyl hydroperoxide (0.44 g dissolved in 5 ml of anhydrous benzene) was added dropwise over 10 minutes. The reaction was refluxed for one additional hour and then cooled to ambient temperature. The benzene was removed in vacuo and the residue chromatographed on silica gel (2% MeOH/CH2Cl2). This yielded a total of 650 mg of diastereomeric products in a 3:1 ratio. Further chromatography resulted in the separation of the diastereomers. The major isomer was a waxy white solid. NMR (CDCl3 /TMS)δ2.60 (d, J=6 Hz, 1H); 3.48 (d, J=6 Hz, 1H); 4.70 (q, J=7 Hz, 2H), 5.25 (s, 1H); 6.8-7.3 (m, 8H); 7.55 (s, 1H); 7.90 (s, 1H).

Workup

  1. temperatureThe solution was then refluxed
  2. temperatureThe reaction was refluxed for one additional hour
  3. customThe benzene was removed in vacuo
  4. customthe residue chromatographed on silica gel (2% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-1bee642fb9574ef99bfcf4dce09e7d96
Source dataset
uspto-grants-1990_12
Patent number
US04980367

Reaction notes

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