tert-Butyl hydroperoxide → HCID 19432964, compound

HRID 1736417Notes

Reaction equation

HRID 1736417 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9](=[CH2:20])[C:10]([C:12]1[CH:13]=[CH:14][C:15]([S:18][CH3:19])=[N:16][CH:17]=1)=[O:11].C([O:25]O)(C)(C)C.CC(C)(CC(C)C)C.[OH-].C([N+](C)(C)C)C1C=CC=CC=1>C1(C)C=CC=CC=1.CO>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1([C:10]([C:12]2[CH:13]=[CH:14][C:15]([S:18][CH3:19])=[N:16][CH:17]=2)=[O:11])[CH2:20][O:25]1

Participants

7

Reactant 4

HCID 6410tert-Butyl hydroperoxideHCID 109072,2,4-TrimethylpentaneHCID 66854Benzyltrimethylammonium hydroxideHCID 19432956HCID 19432956, compound

Product 1

HCID 19432964HCID 19432964, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1140TolueneSolvent

Procedure

A solution of the product of part (iv) (3.8 g, 13 mmol) in toluene (40 ml) was treated with a solution of t-butylhydroperoxide in 2,2,4-trimethylpentane (3M, 4.7ml, 14 mmol) followed by a solution of benzyltrimethylammonium hydroxide in methanol (40%, 100 μl). After 1 hour at room temperature the solvent was removed under reduced pressure. The residue was partitioned between dichloromethane (100 ml) and water (50 ml). The organic phase was separated, dried (MgSO4) and evaporated under reduced pressure to give the title compound as a colourless oil, (3.9 g).

Workup

  1. customAfter 1 hour at room temperature the solvent was removed under reduced pressure
  2. customThe residue was partitioned between dichloromethane (100 ml) and water (50 ml)
  3. customThe organic phase was separated
  4. dry with materialdried (MgSO4)
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-3e4d442ed311427ca88f999176e604ce
Source dataset
uspto-grants-1996_07
Patent number
US05541203

Reaction notes

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