反应详情

Aqueous hydrogen peroxide solution (35%, 3.7 mL) is added dropwise to a solution of {(S)-6-[(R)-7-fluoro-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-indan-1-yloxy]-2,3-dihydro-benzofuran-3-yl}-acetic acid methyl ester (5.0 g) in acetic acid (30 mL) chilled in an ice bath. The solution is stirred with cooling for 0.5 h and at room temperature for another 2 h. Ice-cold water (50 mL) and 2 N aqueous NaOH solution (20 mL) are added, and the mixture is stirred at room temperature overnight. The mixture is extracted with ethyl acetate, and the combined extracts are washed with brine and dried (MgSO4). The solvent is evaporated and the residue is chromatographed on silica gel (cyclohexane/ethyl acetate 80:20→60:40) to give the title compound. LC (method 2): tR=1.01 min; Mass spectrum (ESI+): m/z=359 [M+H]+.

1. temperaturechilled in an ice bath
2. stirringthe mixture is stirred at room temperature overnight
3. extractionThe mixture is extracted with ethyl acetate
4. washthe combined extracts are washed with brine
5. dry with materialdried (MgSO4)
6. customThe solvent is evaporated
7. customthe residue is chromatographed on silica gel (cyclohexane/ethyl acetate 80:20→60:40)