m-Chloroperbenzoic acid → HCID 54150072, compound

HRID 892506Notes

Reaction equation

HRID 892506 reaction equation
[C:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:12][C:11]([CH3:14])([CH3:13])[CH2:10][CH:9]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=3)[C:8]=2[CH:21]=1)(=[O:3])[CH3:2].ClC1C=CC=C(C(OO)=[O:30])C=1>ClCCl>[C:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:12][C:11]([CH3:14])([CH3:13])[CH2:10][CH:9]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][N+:16]=3[O-:30])[C:8]=2[CH:21]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 19895597HCID 19895597, compound

Product 1

HCID 54150072HCID 54150072, compoundYield 7.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

261 mg of 6-acetyl-3,4-dihydro-2,2 -dimethyl-4-(2-pyridyl)-2H-1-benzopyran were dissolved in 20 ml of dichloromethane at room temperature and 250 mg of m-chloroperbenzoic acid were added. After stirring at room temperature for 3 days the mixture was washed in succession with sodium bisulphite solution, sodium bicarbonate solution and water, dried over sodium sulphate and evaporated. The residue was chromatographed on silica gel using 2%-5% (v/v) methanol/chloroform for the elution. The resulting foam was triturated with methylcyclohexane and the solid obtained was recrystallized from t-butyl methyl ether to give 20 mg of 2-(6-acetyl-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-4-yl)pyridine N-oxide of melting point 132°-133° C.

Workup

  1. washwas washed in succession with sodium bisulphite solution, sodium bicarbonate solution and water
  2. dry with materialdried over sodium sulphate
  3. customevaporated
  4. customThe residue was chromatographed on silica gel using 2%-5% (v/v) methanol/chloroform for the elution
  5. customThe resulting foam was triturated with methylcyclohexane
  6. customthe solid obtained
  7. customwas recrystallized from t-butyl methyl ether

Sources & evidence

ORD record
ord-7cfd0731a5544e0698089f8758cff210
Source dataset
uspto-grants-1992_06
Patent number
US05118694

Reaction notes

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