m-Chloroperbenzoic acid → HCID 20030875, compound

HRID 232211Notes

Reaction equation

HRID 232211 reaction equation
[Cl:1][C:2]1([C:15]([O:17][CH:18]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:16])[CH:6](SC2C=CC=CC=2)[CH2:5][C:4](=[O:14])[O:3]1.ClC1C=CC=C(C(OO)=O)C=1>ClCCl>[Cl:1][C:2]1([C:15]([O:17][CH:18]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)=[O:16])[CH:6]=[CH:5][C:4](=[O:14])[O:3]1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 57046507Diphenylmethyl 2-chloro-3-phenylthio-5-oxo-2-tetrahydrofuran carboxylate

Product 1

HCID 20030875HCID 20030875, compoundYield 66.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In 10 ml of dichloromethane was dissolved 0.30 g of the Compound (48) obtained in Example 48. To the solution was added 150 mg of 3-chloroperbenzoic acid. The mixture was stirred at room temperature for 30 minutes. The reaction solution was washed with an aqueous solution of sodium hydrogen carbonate and water, successively. The resultant was dried (Na2SO4), and the solvent was evaporated off. The residue was dissoved in 6 ml of toluene, and the solution was heated at 60° C. for 30 minutes, then the solvent was evaporated off. The residue was subjected to a silica gel column chromatography, followed by elution with hexane-ethyl acetate (5:1) to give 0.15 g of the subject Compound (49) as colorless crystals. Recrystallization from ethyl acetatehexane to give colorless needless, m.p. 99°-101° C.

Workup

  1. washThe reaction solution was washed with an aqueous solution of sodium hydrogen carbonate and water
  2. dry with materialThe resultant was dried (Na2SO4)
  3. customthe solvent was evaporated off
  4. temperaturethe solution was heated at 60° C. for 30 minutes
  5. customthe solvent was evaporated off
  6. washfollowed by elution with hexane-ethyl acetate (5:1)

Sources & evidence

ORD record
ord-a87152415f9f46b0a3060609fbd35de1
Source dataset
uspto-grants-1989_07
Patent number
US04851422

Reaction notes

Loading…