Water → HCID 11600896, compound

To a solution of (5-dimethylamino-benzo[b]thiophen-2-yl)-methanol (790 mg, 3.8 mmol) and triethylamine (4.9 mL, 35.1 mmol) in dimethyl sulfoxide (20 mL) was added a solution of pyridine-sulfur trioxide (1.8 g, 11.2 mmol) in dimethyl sulfoxide (20 mL). The mixture was stirred for 1 hour at room temperature followed by addition of water (50 mL) and ethyl acetate (50 mL). The organic layer was washed with water (3×50 mL) and brine (2×50 mL), dried over anhydrous MgSO4, filtered and concentrated under reduced pressure to give a colourless oil that was purified by flash chromatography (10:90:1 to 50:50:1 ethyl acetate:40-60° C. petroleum ether:triethylamine) to give a solid that was recrystallised from ethanol to give the title compound (743 mg, 95%) as a solid, mp 105-106° C.

1. washThe organic layer was washed with water (3×50 mL) and brine (2×50 mL)
2. dry with materialdried over anhydrous MgSO4
3. filtrationfiltered
4. concentrationconcentrated under reduced pressure
5. customto give a colourless oil that
6. customwas purified by flash chromatography (10:90:1 to 50:50:1 ethyl acetate:40-60° C. petroleum ether:triethylamine)
7. customto give a solid
8. customthat was recrystallised from ethanol

ORD record

ord-6c3750a2f4a54cdeb3c7306bf71c7928

Source dataset

uspto-grants-2010_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07683185B2