Sodium Thiosulfate → 3,3a,4,5-tetrahydro-7H-pyrano[3,4-c]isoxazole

HRID 217969Notes

Reaction equation

HRID 217969 reaction equation
Cl[O-].[Na+].[CH2:4]([O:8][CH2:9][CH:10]=[N:11][OH:12])[CH2:5][CH:6]=[CH2:7].S([O-])([O-])(=O)=S.[Na+].[Na+]>ClCCl>[N:11]1[O:12][CH2:7][CH:6]2[CH2:5][CH2:4][O:8][CH2:9][C:10]=12

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 23665760Sodium HypochloriteHCID 72245372HCID 72245372, compound

Product 1

HCID 574756753,3a,4,5-tetrahydro-7H-pyrano[3,4-c]isoxazoleYield 79.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 5% sodium hypochlorite solution (122 ml) was added dropwise to a solution of 3-butenyloxyacetaldehyde oxime (5.30 g) in dichloromethane (530 ml) under ice-cooling. After stirring at the same temperature for two hours, sodium thiosulfate was added. The aqueous layer was extracted with dichloromethane. The organic layers were combined and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography to obtain the title compound (4.15 g).

Workup

  1. temperaturecooling
  2. extractionThe aqueous layer was extracted with dichloromethane
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-1ec50fdb46244331b3fe18e2c88fc895
Source dataset
uspto-grants-2012_06
Patent number
US08198269B2

Reaction notes

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