Tetrahydrofuran → HCID 59215205, compound

Temperature

55 °C

A solution 3-(6-chloropyridin-3-yl)-2-methylpropyl-4-methyl-benzenesulfonate (5.0 g, 14.7 mmol) and sodium methylthiolate (2.10 g, 30 mmol) in THF (50 mL) was stirred overnight at room temperature. The remaining unreacted starting material indicated on TLC was converted into the product completely after the solution was heated at 55° C. for 4 more hours. The mixture was diluted with ether and washed with 2 N NaOH solution (50 mL). The aqueous phase was washed with ether (50 mL). The combined organic phase was washed with brine (50 mL), dried over MgSO4, filtered and concentrated to give 2.94 g of the desired crude sulfide in 93% yield as a yellowish oil: M+=215, 217; δ 2.07 (s, 3H), 0.95 (d, 3H).

1. washwashed with 2 N NaOH solution (50 mL)
2. washThe aqueous phase was washed with ether (50 mL)
3. washThe combined organic phase was washed with brine (50 mL)
4. dry with materialdried over MgSO4
5. filtrationfiltered
6. concentrationconcentrated

ORD record

ord-64bf707af23644e2a6fca67d9e1bd514

Source dataset

uspto-grants-2011_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07897782B2