Ethyl Acetate → HCID 90060321, compound

HRID 1779190Notes

Reaction equation

HRID 1779190 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10].[S:14]([O-:17])([O-])=[O:15].[Na+].[Na+].S(Cl)([Cl:22])=O.C(OCC)(=O)C>C(O)C.O>[Cl:22][S:14]([CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])(=[O:17])=[O:15]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 24386Thionyl ChlorideHCID 24437Sodium SulfiteHCID 264813Ethyl 8-bromooctanoate

Product 1

HCID 90060321HCID 90060321, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

At room temperature, ethyl 8-bromo-octanoate (753.5 mg, 3.00 mmol) was dissolved in ethanol (1.88 mL), and a solution of sodium sulfite (718.4 mg, 5.70 mmol) in water (2.64 mL) was added. The mixture was then stirred under reflux for 2 hours, and cooled to room temperature. The solvent was then distilled off under reduced pressure. To the residue was added ethanol, and the solvent was again distilled off under reduced pressure. The residue was dried in an oil bath at 60° C. under reduced pressure, and toluene (11.3 mL) and DMF (10 μL) were then added at room temperature. Thionyl chloride (2.16 mL, 30.0 mmol) was added dropwise. The mixture was then stirred under reflux for 6 hours and cooled to room temperature. The progress of the reaction was then stopped by adding water. Ethyl acetate was added, and the mixture was extracted. The organic layer was washed with water and a saturated brine, dried over anhydrous sodium sulfate, and filtered. The solvent was distilled off. The resulting residue was then purified with SP1 (SiO2 cartridge, 10% ethyl acetate/n-hexane, Rf=0.2) to obtain ethyl 8-chlorosulfonyl-octanoate (No. 6804260; 692.3 mg, 85% yield).

Workup

  1. temperatureunder reflux for 2 hours
  2. distillationThe solvent was then distilled off under reduced pressure
  3. additionTo the residue was added ethanol
  4. distillationthe solvent was again distilled off under reduced pressure
  5. dry with materialThe residue was dried in an oil bath at 60° C. under reduced pressure, and toluene (11.3 mL) and DMF (10 μL)
  6. additionwere then added at room temperature
  7. stirringThe mixture was then stirred
  8. temperatureunder reflux for 6 hours
  9. temperaturecooled to room temperature
  10. extractionthe mixture was extracted
  11. washThe organic layer was washed with water
  12. dry with materiala saturated brine, dried over anhydrous sodium sulfate
  13. filtrationfiltered
  14. distillationThe solvent was distilled off
  15. customThe resulting residue was then purified with SP1 (SiO2 cartridge, 10% ethyl acetate/n-hexane, Rf=0.2)

Sources & evidence

ORD record
ord-5f08554000284b458e407b4b3c2c7b33
Source dataset
uspto-grants-2016_02
Patent number
US09266853B2

Reaction notes

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