Ethyl Acetate → HCID 90060321, compound

Participants

Reaction Steps

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).

Provenance & Evidence