Trifluoroacetic acid → HCID 59595882, compound

To a solution of 4-(benzofuran-5-yl)-tetrahydro-2H-pyran-4-ol (109 mg, 0.5 mmol) in DCM (5 mL) at 0° C. under nitrogen atmosphere was added triethylsilane (175 mg, 1.5 mmol) followed by TFA (570 mg, 5.0 mmol). After stirring for 15 min at the same temperature, the cooling bath was removed, and allowed the reaction mixture to reach room temperature. It was further stirred at room temperature for 6 h and then poured into crushed ice-water mixture (10 mL). It was extracted with DCM (3×10 mL), and the combined organic layer was washed with brine (10 mL), dried and evaporated. The crude compound was purified by column chromatography using 5% EtOAc-hexanes to afford the desired product (88%). 1H NMR (400 MHz, CDCl3) δ 7.61 (d, 1H), 7.44 (d, 2H), 7.15 (d, 1H), 6.73 (d, 1H), 4.11 (dd, 2H), 3.56 (t, 2H), 2.89-2.81 (m, 1H), 1.93-1.79 (m, 4H).

1. customthe cooling bath was removed
2. customto reach room temperature
3. stirringIt was further stirred at room temperature for 6 h
4. additionpoured
5. custominto crushed ice-water mixture (10 mL)
6. extractionIt was extracted with DCM (3×10 mL)
7. washthe combined organic layer was washed with brine (10 mL)
8. customdried
9. customevaporated
10. customThe crude compound was purified by column chromatography

ORD record

ord-f44c1b836db042178ab0b2d69b466fed

Source dataset

uspto-grants-2011_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07919519B2