m-Chloroperbenzoic acid → HCID 72410012, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of Compound 239D (25.2 g, 88.3 mmol) in 250 mL of CH2Cl2 at 0° C. was added solid m-CPBA (39.6 g, 176.6 mmol, 77% max) in small portions while the internal temperature was kept below 0° C. during the addition. The mixture was stirred at 0° C. for 30 min and then room temperature for 4.0 hrs. More solid m-CPBA (39.6 g, 176.6 mmol, 77% max) was added in small portions and the mixture was stirred at room temperature for three days. The precipitate was removed by filtration and the filtrate was washed with 20% Na2S2O3 (500 mL×3), sat'd NaHCO3 (500 mL×3) and brine (250 mL), dried over anhydrous Na2SO4. Purification by flash chromatography (hexane-EtOAc: 9.5:0.5 to 9:1) on silica gel afforded 4.33 g of 239E (lower Rf) as an oil.

Provenance & Evidence