m-Chloroperbenzoic acid → HCID 69801129, compound

HRID 1816591Notes

Reaction equation

HRID 1816591 reaction equation
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]([O:10]O)=[O:9])[CH:3]=1.[CH:12]([O:15][CH:16]([CH2:22][C:23]1[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=1)[C:17]([O:19][CH2:20][CH3:21])=[O:18])([CH3:14])[CH3:13]>ClCCl.C(=O)([O-])O.[Na+]>[C:8]([O-:10])(=[O:9])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:2][CH2:3][CH2:4]/[CH:3]=[CH:2]\[CH2:7][CH2:6][CH2:27][CH2:28][CH2:23][CH2:22][CH2:16][CH3:17].[CH2:20]([O:19][C:17](=[O:18])[CH:16]([O:15][CH:12]([CH3:14])[CH3:13])[CH2:22][C:23]1[CH:24]=[CH:25][NH+:26]=[CH:27][CH:28]=1)[CH3:21]

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 22494133HCID 22494133, compound

Product 1

HCID 69801129HCID 69801129, compoundYield 119.8%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

6.0 g of m-chloroperbenzoic acid was added to a solution of 4.88 g ethyl 2-isopropoxy-3-(4-pyridyl)propanoate in dichloromethane (50 mL), followed by stirring at room temperature for 1.5 hours. After the reaction solution was diluted with saturated aqueous sodium hydrogencarbonate solution, the aqueous layer was extracted with dichloromethane for 3 times. The combined organic layer was dried over anhydrous sodium sulfate and then concentrated, to give 6.40 g crude 4-(3-ethoxy-2-isopropoxy-3-oxopropyl)-1-pyridinium oleate as a yellow oil.

Workup

  1. extractionthe aqueous layer was extracted with dichloromethane for 3 times
  2. dry with materialThe combined organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-32c0ad75e1a344c8abb11f739e7a6914
Source dataset
uspto-grants-2005_04
Patent number
US06884821B1

Reaction notes

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