Tetrahydrofuran → HCID 71090391, compound

Participants

Reaction Steps

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.

Provenance & Evidence