m-Chloroperbenzoic acid → HCID 54523856, compound

HRID 1073895Notes

Reaction equation

HRID 1073895 reaction equation
[C:1]([C:9]1[CH:10]=[CH:11][C:12]2[O:17][C:16]([CH3:19])([CH3:18])[CH2:15][CH:14]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=3)[C:13]=2[CH:26]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClC1C=CC=C(C(OO)=[O:35])C=1>ClCCl>[C:1]([C:9]1[CH:10]=[CH:11][C:12]2[O:17][C:16]([CH3:19])([CH3:18])[CH2:15][CH:14]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][N+:21]=3[O-:35])[C:13]=2[CH:26]=1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 19895648HCID 19895648, compound

Product 1

HCID 54523856HCID 54523856, compoundYield 20.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

94 mg of 6-benzoyl-3,4-dihydro-2,2-dimethyl-4-(2-pyridyl)-2H-1-benzopyran and 52 mg of m-chloroperbenzoic acid were stirred in 15 ml of dichloromethane at room temperature until thin-layer chromatography indicated that the reaction was complete. The mixture was washed in succession with sodium bisulphite solution and sodium bicarbonate solution, then dried over sodium sulphate and evaporated. The residue was chromatographed on silica gel using 10% (v/v) methanol/ethyl acetate for the elution. After trituration with diethyl ether there were obtained 20 mg of 2-(6-benzoyl-3,4-dihydro-2,2-dimethyl-2H-1-benzo-pyran-4-yl)pyridine N-oxide of melting point 134°-136° C.

Workup

  1. washThe mixture was washed in succession with sodium bisulphite solution and sodium bicarbonate solution
  2. dry with materialdried over sodium sulphate
  3. customevaporated
  4. customThe residue was chromatographed on silica gel using 10% (v/v) methanol/ethyl acetate for the elution

Sources & evidence

ORD record
ord-50087536a9054d11a9f75662dccdbc6c
Source dataset
uspto-grants-1990_11
Patent number
US04971982

Reaction notes

Loading…