1-Dodecanethiol → HCID 131734536, compound

Temperature

0 °C

To a solution of 1-dodecanethiol (3.38 mL) in toluene (5.0 mL) was added aluminum chloride (627 mg) at 0° C. After being stirred at 0° C. for 50 min, to the solution was added a mixture of methyl(4-chloro-6-methoxy-2-methyl-1-benzothiophen-3-yl)acetate (670 mg) in toluene (10 mL) at 0° C. The mixture was stirred at 80° C. for 14 h. To the suspension was added aluminum chloride (627 mg) again. The mixture was stirred at 80° C. for 5 h. The mixture was quenched with water and 1N HCl, and extracted with EtOAc. The organic layer was washed with brine, dried over MgSO4, and concentrated in vacuo. The residue was dissolved in MeOH (2.0 mL), and to the solution was added conc.H2SO4 (0.025 mL). The mixture was stirred at 80° C. for 2 h. The mixture was concentrated and the residue was neutralized with saturated aqueous NaHCO3 and extracted with EtOAc. The combined organic layer was washed with brine, dried over MgSO4, and concentrated in vacuo. The solid was washed with hexane to give the title compound (557.8 mg).

1. additionwas added
2. stirringThe mixture was stirred at 80° C. for 14 h
3. stirringThe mixture was stirred at 80° C. for 5 h
4. customThe mixture was quenched with water and 1N HCl
5. extractionextracted with EtOAc
6. washThe organic layer was washed with brine
7. dry with materialdried over MgSO4
8. concentrationconcentrated in vacuo
9. dissolutionThe residue was dissolved in MeOH (2.0 mL)
10. additionto the solution was added conc
11. stirringThe mixture was stirred at 80° C. for 2 h
12. concentrationThe mixture was concentrated
13. extractionextracted with EtOAc
14. washThe combined organic layer was washed with brine
15. dry with materialdried over MgSO4
16. concentrationconcentrated in vacuo
17. washThe solid was washed with hexane

ORD record

ord-4a384ae9dca7423fa07c3d95923e4710

Source dataset

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09238639B2