Di-tert-butyl peroxide → HCID 178445808, compound

HRID 2404156Notes

Reaction equation

HRID 2404156 reaction equation
C([O:5]OC(C)(C)C)(C)(C)C.[Se](=O)=O.[C:14]([CH:18]1[CH2:23][CH2:22][CH:21]([O:24][C:25]2[CH:26]=[C:27]3[C:32](=[CH:33][CH:34]=2)[N:31]=[C:30]([CH3:35])[CH:29]=[C:28]3[C:36]([F:39])([F:38])[F:37])[CH2:20][CH2:19]1)([CH3:17])([CH3:16])[CH3:15]>O1CCOCC1>[C:14]([C@H:18]1[CH2:23][CH2:22][C@H:21]([O:24][C:25]2[CH:26]=[C:27]3[C:32](=[CH:33][CH:34]=2)[N:31]=[C:30]([CH:35]=[O:5])[CH:29]=[C:28]3[C:36]([F:39])([F:37])[F:38])[CH2:20][CH2:19]1)([CH3:17])([CH3:15])[CH3:16]

Participants

5

Reactant 3

HCID 8033Di-tert-butyl peroxideHCID 24007Selenium DioxideHCID 66926809HCID 66926809, compound

Product 1

HCID 178445808HCID 178445808, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
50 °C

Procedure

Di-tert-butyl peroxide (0.186 mL, 1.01 mmol) was added to a suspension of Selenium dioxide (0.252 g, 2.27 mmol) in 1,4-Dioxane (6.0 mL). The mixture was stirred for 30 minutes, then 6-(4-tert-Butyl-cyclohexyloxy)-2-methyl-4-trifluoromethyl-quinoline (0.366 g, 1.00 mmol) was added as a solution in 1,4-Dioxane (2.0 mL). The mixture was sealed and was heated at 50° C. for 20 h. The reaction was filtered through Celite and washed with dioxane. The solvent was evaporated and the residue was purified on silica gel column using 0-20% ethyl acetate in hexanes as eluent. Isolated was (Rf=0.70 in 3:1 hexanes/ethyl acetate) the product (212 mg, 56%). ESI-MS (M+H+): 380.20.

Workup

  1. customThe mixture was sealed
  2. filtrationThe reaction was filtered through Celite
  3. washwashed with dioxane
  4. customThe solvent was evaporated
  5. customthe residue was purified on silica gel column
  6. customIsolated

Sources & evidence

ORD record
ord-6215266eaa05402da7e71f15dff7a0ef
Source dataset
uspto-grants-2014_08
Patent number
US08802659B2

Reaction notes

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