Tetrahydrofuran → Methyl 3-[(4-methoxy)-tetrahydropyran-4-yl]phenyl-methylthioacetate

Temperature

5 °C

A solution of 3-[(4-methoxy)tetrahydropyran-4-yl]-α-bromotoluene (1.0 g, 3.87 mmol) in 10 mL of anhydrous THF was cooled to 5° C. A solution of methyl thioglycolate (0.41 g, 3.87 mmol) and DBU (0.59 g, 3.87 mmol) in 10 mL of THF was added while maintaining the temperature at 5° C. The reaction mixture was stirred for 2 h at room temperature. The reaction mixture was diluted with 250 mL of ethyl acetate, and the organic layer was washed with 1 N HCl (2×100 mL), saturated sodium bicarbonate (1×100 mL), brine (1×100 mL), dried over magnesium sulfate, filtered and concentrated. The concentrated residue was purified by flash column chromatography on silica gel, eluting with 40% ethyl acetate in hexane, to give 0.87 g (72%) of methyl 3-[(4-methoxy)-tetrahydropyran-4-yl]phenyl-methylthioacetate as a clear oil: 1H NMR (CDCl3/300 MHz) δ 1.94–2.09 (m, 4H), 2.97 (s, 3H), 3.08 (s, 2H), 3.73 (s, 3H), 3.77–3.92 (m, 6H), 7.26–7.36 (m, 4H). HRMS calcd for C16H22O4S 311.1317. Found 311.1271.

1. washthe organic layer was washed with 1 N HCl (2×100 mL), saturated sodium bicarbonate (1×100 mL), brine (1×100 mL)
2. dry with materialdried over magnesium sulfate
3. filtrationfiltered
4. concentrationconcentrated
5. customThe concentrated residue was purified by flash column chromatography on silica gel
6. washeluting with 40% ethyl acetate in hexane

ORD record

ord-ab3d773fcea24c38ae33939cc7a0eae7

Source dataset

uspto-grants-2006_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06998415B2