Tetrahydrofuran → HCID 71090391, compound

To a solution of 6-[tert-butyl(dimethyl)silyl]oxy-1-(trifluoromethyl)-3H-isobenzofuran-1-ol (Intermediate 26, 1.2 g, 3.59 mmol) in DCM (20 mL) 2,2,2-trifluoroacetic acid (5.5 ml, 71.77 mmol) and then triethylsilane (2.86 ml, 17.94 mmol) were added and the reaction mixture was stirred for 1 hour at room temperature. The reaction was diluted with DCM (50 ml) and water (30 ml) and two phases were separated. The organic layer was washed with brine (2×20 ml), dried (Na2SO4), filtered and evaporated. The residue was dissolved in THF (20 mL) and tetrabutylammonium fluoride 1M in THF (3.6 ml, 3.6 mmol) was added. The reaction mixture was stirred for 1 hour at room temperature. The reaction was diluted with an aqueous saturated solution of NH4Cl (30 ml) and extracted with ethyl acetate (2×30 ml). The organic layer was dried (Na2SO4), filtered and evaporated and the residue was purified by flash chromatography (Biotage system) on silica gel using a SNAP 25 g as column and cyclohexane/ethyl acetate from 100:0 to 70:30 as eluent affording the title compound (550 mg) as colourless oil.

1. customwere separated
2. washThe organic layer was washed with brine (2×20 ml)
3. dry with materialdried (Na2SO4)
4. filtrationfiltered
5. customevaporated
6. dissolutionThe residue was dissolved in THF (20 mL)
7. stirringThe reaction mixture was stirred for 1 hour at room temperature
8. extractionextracted with ethyl acetate (2×30 ml)
9. dry with materialThe organic layer was dried (Na2SO4)
10. filtrationfiltered
11. customevaporated
12. customthe residue was purified by flash chromatography (Biotage system) on silica gel using a SNAP 25 g as column and cyclohexane/ethyl acetate from 100:0 to 70:30 as eluent

ORD record

ord-5862444ba6ab47a09a03e2d186f0dde5

Source dataset

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09193704B2