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0 °C

6-Vinyl-3,4-dihydro-1H-isochromen-1-one (36.0 g, 207 mmol, 1.0 eq) was added into a 500 mL round bottom flask and dissolved in dichloromethane (500 mL). The solution was cooled to 0° C., added portion wise 3-chloroperoxybenzoic acid (98.0 g, 413 mmol, 2.0 eq). The mixture was then purged with N2 and stirred at r.t. for 18 hr. To above solution was added water (100 mL). The crude product was extracted with dichloromethane. The organic phase was washed with brine (100 mL), dried over anhydrous Na2SO4, filtered, concentrated and purified by flash column chromatography (hexane/EtOAc 0-50%). The desired product was obtained. LC-MS (IE, m/z): 191.27 [M+1]+; 1H NMR (500 MHz, CDCl3, δ in ppm): 8.07 (1H, aromatic, d, J=8.1 Hz), 7.32 (1H, aromatic, d, J=8.0 Hz), 7.16 (1H, br-s, aromatic), 4.52 (2H, CH2—O—, t, J=5.7 Hz), 3.90 (1H, br-s), 3.20 (1H, m), 3.05 (2H, CH2—CH2—O—, t, J=5.7 Hz), 2.77 (1H, m).

1. customThe mixture was then purged with N2
2. additionTo above solution was added water (100 mL)
3. extractionThe crude product was extracted with dichloromethane
4. washThe organic phase was washed with brine (100 mL)
5. dry with materialdried over anhydrous Na2SO4
6. filtrationfiltered
7. concentrationconcentrated
8. custompurified by flash column chromatography (hexane/EtOAc 0-50%)