Selenium Dioxide → HCID 58130334, compound

HRID 1515363Notes

Reaction equation

HRID 1515363 reaction equation
[CH3:1][C:2]1[S:3][C:4]2[C:9]([C:10](=[O:18])[C:11]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[CH:8][CH:7]=[CH:6][CH:5]=2.[Se](=O)=[O:20].C(=O)([O-])O.[Na+].[BH4-].[Na+].[Cl-].[NH4+]>ClC1C=CC=CC=1.CO>[OH:20][CH2:1][C:2]1[S:3][C:4]2[C:9]([C:10](=[O:18])[C:11]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[CH:8][CH:7]=[CH:6][CH:5]=2

Participants

8

Reactant 5

HCID 24007Selenium DioxideHCID 25517Ammonium ChlorideHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 58130396HCID 58130396, compound

Product 1

HCID 58130334HCID 58130334, compoundYield 38%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 7964ChlorobenzeneSolvent

Conditions

Temperature
0 °C

Procedure

The compound (1.0 mmol, 252 mg) obtained in (2) above and selenium dioxide (1.2 mmol, 133 mg) were dissolved in 5 mL of chlorobenzene, and the solution was refluxed under a nitrogen atmosphere for 12 hours. After the disappearance of the starting materials was confirmed by NMR, the temperature of the solution was returned to room temperature, and a saturated aqueous sodium hydrogen carbonate solution was poured thereinto to terminate the reaction. Then, the organic layer extracted with methylene chloride was dried over magnesium sulfate, and the solvents were distilled off under reduced pressure. The residue was passed through a silica gel column, and directly used in the subsequent reaction. The obtained mixture was dissolved in 2 mL of methanol, to which sodium borohydride (1.0 mmol, 38 mg) was added; and under a nitrogen atmosphere, the resulting product was stirred at 0° C. for 2 hours. Then, a saturated aqueous ammonium chloride solution was added thereto to terminate the reaction. Afterward, the organic substances were extracted with ethyl acetate, the obtained organic layer was dried over magnesium sulfate, and the solvents were evaporated under reduced pressure. The residue was purified by silica gel column chromatography, and recrystallized with hexane/ethyl acetate. Thereby, the title compound (0.38 mmol, 104 mg) was obtained in a two-step yield of 38%.

Workup

  1. temperaturethe solution was refluxed under a nitrogen atmosphere for 12 hours
  2. customwas returned to room temperature
  3. customto terminate
  4. customthe reaction
  5. extractionThen, the organic layer extracted with methylene chloride
  6. dry with materialwas dried over magnesium sulfate
  7. distillationthe solvents were distilled off under reduced pressure
  8. customdirectly used in the subsequent reaction
  9. additionwas added
  10. customto terminate
  11. customthe reaction
  12. extractionAfterward, the organic substances were extracted with ethyl acetate
  13. dry with materialthe obtained organic layer was dried over magnesium sulfate
  14. customthe solvents were evaporated under reduced pressure
  15. customThe residue was purified by silica gel column chromatography
  16. customrecrystallized with hexane/ethyl acetate

Sources & evidence

ORD record
ord-ae513f09a3d14b7e8bdb991da112b1ba
Source dataset
uspto-grants-2012_07
Patent number
US08222429B2

Reaction notes

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