m-Chloroperbenzoic acid → HCID 54215893, compound

HRID 892507Notes

Reaction equation

HRID 892507 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[C:20]([CH3:21])=[CH:19][CH:18]=[CH:17][N:16]=3)[C:8]=2[CH:22]=1)(=[O:3])[CH3:2].ClC1C=CC=C(C(OO)=[O:31])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[C:20]([CH3:21])=[CH:19][CH:18]=[CH:17][N+:16]=3[O-:31])[C:8]=2[CH:22]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 19895658HCID 19895658, compound

Product 1

HCID 54215893HCID 54215893, compoundYield 26.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

101 mg of 6-acetyl-3,4-dihydro-2,2-dimethyl-4-(3-methyl-2-pyridyl)-2H-1-benzopyran were dissolved in 5 ml of dichloromethane at room temperature and 91 mg of m-chloroperbenzoic acid were added. After 1 hour the mixture was washed in succession with sodium bisulphite solution, sodium bicarbonate solution and water. The organic extract was dried over sodium sulphate and evaporated to give an oil. This oil was triturated with t-butyl methyl ether to give a solid which, after recrystallization from ethyl acetate/t-butyl methyl ether, gave 28 mg of 2-(6-acetyl-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-4-yl)-3-methylpyridine N-oxide of melting point 154°-156° C.

Workup

  1. washAfter 1 hour the mixture was washed in succession with sodium bisulphite solution, sodium bicarbonate solution and water
  2. extractionThe organic extract
  3. dry with materialwas dried over sodium sulphate
  4. customevaporated
  5. customto give an oil
  6. customThis oil was triturated with t-butyl methyl ether
  7. customto give a solid which
  8. customafter recrystallization from ethyl acetate/t-butyl methyl ether

Sources & evidence

ORD record
ord-1519956922e2441c9bf1fc295b54b7fc
Source dataset
uspto-grants-1992_06
Patent number
US05118694

Reaction notes

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