m-Chloroperbenzoic acid → HCID 15280201, compound

HRID 1492470Notes

Reaction equation

HRID 1492470 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[C:12]([O:20][CH2:21][C@@H:22]1[C@@H:27]([CH2:28][O:29][C:30](=[O:37])[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH2:26][CH:25]=[CH:24][CH2:23]1)(=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.S([O-])(O)=O.[Na+].C(=O)([O-])O.[Na+]>C(Cl)Cl.CCCCCC>[C:30]([O:29][CH2:28][C@@H:27]1[C@@H:22]([CH2:21][O:20][C:12](=[O:19])[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:23][CH:24]2[CH:25]([O:9]2)[CH2:26]1)(=[O:37])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

7

Reactant 4

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 10760318HCID 10760318, compoundHCID 23665763Sodium Bisulfite

Product 1

HCID 15280201HCID 15280201, compoundYield 93.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8058HexaneSolvent

Procedure

m-Chloroperbenzoic acid (777 mg, 4.5 mmoles) was added to a solution of (4S,5S)-4,5-bis(benzoyloxymethyl)-1-cyclohexene (1.05 g, 3.0 mmoles) in methylene chloride (6 ml) under cooling with ice. After stirring the mixture at room temperature for 2 hours, a saturated aqueous solution of sodium hydrogen sulfite was added to the reaction mixture and the excessive peracid was decomposed, after which a saturated aqueous solution of sodium hydrogen carbonate was added and the whole mixture was subjected to extraction with ethyl ether. The ether extract solution was washed with water and then with saturated aqueous solution of sodium hydrogen carbonate, and dried on anhydrous sodium sulfate. After distilling off the solvent therefrom under reduced pressure, the residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:3, v/v) to obtain (3S,4S)-3,4-bis(benzoyloxymethyl)-7-oxabicyclo[4.1.0]heptane (1.025 g, Yield 93%).

Workup

  1. temperatureunder cooling with ice
  2. extractionthe whole mixture was subjected to extraction with ethyl ether
  3. extractionThe ether extract solution
  4. washwas washed with water
  5. dry with materialwith saturated aqueous solution of sodium hydrogen carbonate, and dried on anhydrous sodium sulfate
  6. distillationAfter distilling off the solvent
  7. customunder reduced pressure, the residue was purified by silica gel column chromatography (ethyl acetate

Sources & evidence

ORD record
ord-e2705e36c2b64bd8b4e56b3f93b05f71
Source dataset
uspto-grants-1994_12
Patent number
US05374625

Reaction notes

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