Methanol → HCID 85848392, compound

Participants

Reaction Conditions

Reaction Steps

Under a nitrogen atmosphere, 8-heptylsulfanyl-octanoic acid (No. 6804237; 2.04 g, 7.43 mmol) was dissolved in methanol (20.4 mL), and the mixture was cooled to 0° C. While maintaining the temperature at 0° C., thionyl chloride (589.5 μL, 8.18 mmol) was added. The mixture was stirred at 0° C. for 5.0 minutes and at room temperature for 4.0 hours. The solvent was distilled off under reduced pressure. Methanol was then added to the residue, and the solvent was again distilled off under reduced pressure. This operation was repeated twice. To the residue was added dichloromethane. The organic layer was washed with water and a saturated brine in order, 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=0.5) to obtain methyl 8-heptylsulfanyl-octanoate (No. 6804238; 2.29 g, quant.).

Provenance & Evidence