Hydrochloric Acid → HCID 89690298, compound

A mixture of 2-(4,5-difluoro-2-thienyl)-1,3-dioxolane (586 mg), THF (10 ml) and 6 M HCl (1 ml) was stirred at ambient temperature for 1 h. The mixture was quenched with saturated NaHCO3 solution and extracted with EtOAc. The organic layer was separated, washed with water and brine successively, dried over MgSO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography (hexane/EtOAc). The resulting oil was dissolved in THF (10 ml), and NaBH4 (48.5 mg) and MeOH (0.1 ml) were added to the solution at room temperature. After the mixture was stirred at room temperature for 15 min, the mixture was poured into saturated NH4Cl solution and extracted with EtOAc. The organic layer was separated, washed with water and brine successively, dried over MgSO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography (hexane/EtOAc) to give the title compound (190 mg) as a mixture with (4-bromo-2-thienyl)methanol and (4-bromo-5-fluoro-2-thienyl)methanol.

1. customThe mixture was quenched with saturated NaHCO3 solution
2. extractionextracted with EtOAc
3. customThe organic layer was separated
4. washwashed with water and brine successively
5. dry with materialdried over MgSO4
6. concentrationconcentrated in vacuo
7. customThe residue was purified by silica gel column chromatography (hexane/EtOAc)
8. dissolutionThe resulting oil was dissolved in THF (10 ml)
9. additionNaBH4 (48.5 mg) and MeOH (0.1 ml) were added to the solution at room temperature
10. stirringAfter the mixture was stirred at room temperature for 15 min
11. additionthe mixture was poured into saturated NH4Cl solution
12. extractionextracted with EtOAc
13. customThe organic layer was separated
14. washwashed with water and brine successively
15. dry with materialdried over MgSO4
16. concentrationconcentrated in vacuo
17. customThe residue was purified by silica gel column chromatography (hexane/EtOAc)

ORD record

ord-47227ca6830d43bf8ba90fe9a571e9b0

Source dataset

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09365540B2