m-Chloroperbenzoic acid → HCID 86743003, compound

HRID 1761779Notes

Reaction equation

HRID 1761779 reaction equation
[C:1](/[CH:4]=[C:5](\[CH3:24])/[CH2:6][CH2:7]/[CH:8]=[C:9](\[CH3:23])/[CH2:10][CH2:11][C:12](=[O:22])[CH:13]([CH3:21])[CH2:14][S:15][CH2:16][C:17]([O:19][CH3:20])=[O:18])(=[O:3])[NH2:2].ClC1C=CC=C(C(OO)=[O:33])C=1>C(Cl)Cl>[C:1](/[CH:4]=[C:5](\[CH3:24])/[CH2:6][CH2:7]/[CH:8]=[C:9](\[CH3:23])/[CH2:10][CH2:11][C:12](=[O:22])[CH:13]([CH3:21])[CH2:14][S:15]([CH2:16][C:17]([O:19][CH3:20])=[O:18])=[O:33])(=[O:3])[NH2:2]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 86743002HCID 86743002, compound

Product 1

HCID 86743003HCID 86743003, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 500 mg (0.0014 mol) of methyl [[(6E,10E)-11-carbamoyl-2,6,10-trimethyl-3-oxo-6,10-undecadienyl]thio]acetate in 30 ml of methylene chloride is treated at 0° with 270 mg of m-chloroperbenzoic acid. The solution is stirred at 0° for 1 hour under argon. The reaction solution is washed with aqueous potassium carbonate solution. After drying and removing the solvent the residue is chromatographed on silica gel with ether-methanol 3:1. There is obtained methyl [[(6E,10E)-11-carbamoyl-2,6,10-trimethyl-3-oxo-6,10-undecadienyl]sulfinyl]acetate which exhibits the following absorption bands in the IR spectrum: 3329 cm-1, 3197 cm-1, 1734 cm-1, 1671 cm-1, 1639 cm-1, 1610 cm-1, 1439 cm-1, 1307 cm-1, 1218 cm-1, 1193 cm-1, 1148 cm-1, 1016 cm- 1.

Workup

  1. washThe reaction solution is washed with aqueous potassium carbonate solution
  2. customAfter drying
  3. customremoving the solvent the residue
  4. customis chromatographed on silica gel with ether-methanol 3:1

Sources & evidence

ORD record
ord-e40067d4189c4ad4af386e1bfe69c834
Source dataset
uspto-grants-1989_05
Patent number
US04827004

Reaction notes

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