Methanol → HCID 85848392, compound

Temperature

0 °C

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.).

1. temperatureWhile maintaining the temperature at 0° C.
2. distillationThe solvent was distilled off under reduced pressure
3. additionMethanol was then added to the residue
4. distillationthe solvent was again distilled off under reduced pressure
5. additionTo the residue was added dichloromethane
6. washThe organic layer was washed with water
7. dry with materiala saturated brine in order, dried over anhydrous sodium sulfate
8. filtrationfiltered
9. distillationThe solvent was distilled off
10. customThe resulting residue was then purified with SP1 (SiO2 cartridge, 10% ethyl acetate/n-hexane, Rf=0.5)

ORD record

ord-5361de37238146ec8ab2f75b394ab564

Source dataset

uspto-grants-2016_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09266853B2