3-butylthiolane → 3-Butyl-1lambda~4~-thiolan-1-one

HRID 1979749Notes

Reaction equation

HRID 1979749 reaction equation
I([O-])(=O)(=O)=[O:2].[Na+].[CH2:7]([CH:11]1[CH2:15][S:14][CH2:13][CH2:12]1)[CH2:8][CH2:9][CH3:10]>O>[CH2:7]([CH:11]1[CH2:15][S:14](=[O:2])[CH2:13][CH2:12]1)[CH2:8][CH2:9][CH3:10]

Participants

4

Reactant 2

HCID 5681133-butylthiolaneHCID 23667635Sodium periodate

Product 1

HCID 33632513-Butyl-1lambda~4~-thiolan-1-oneYield 62.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Sodium metaperiodate (4.1 g, 0.019 mole) was dissolved in 40 ml of water and cooled in an ice bath. 3-Butyltetramethylene sulfide (2.62 g, 0.018 mole) was added and the reaction mixture was stirred at 0° overnight. The NaIO3 which precipitated during the reaction was removed by filtration, and the filtrate was extracted with two 40-ml portions of chloroform. The extract was dried over anhydrous MgSO4, and the solvent was removed under reduced pressure. Vacuum distillation yielded 1.8 g (62%) of 3-butyltetramethylene sulfoxide: b.p. 95° C. C/0.52 mm. Anal. Calcd. for C8H16SO; C, 59.95, H, 10.06; S, 20.00. Found: C, 59.78; H, 10.05, S, 1972%. The NMR spectrum is consistent with the structure for 3-butyltetramethylene sulfoxide.

Workup

  1. temperaturecooled in an ice bath
  2. customThe NaIO3 which precipitated during the reaction
  3. customwas removed by filtration
  4. extractionthe filtrate was extracted with two 40-ml portions of chloroform
  5. dry with materialThe extract was dried over anhydrous MgSO4
  6. customthe solvent was removed under reduced pressure
  7. distillationVacuum distillation

Sources & evidence

ORD record
ord-bd0097aa24f54c0ba8b9d7d540d62299
Source dataset
uspto-grants-1984_11
Patent number
US04482568

Reaction notes

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