Sodium Thiosulfate → HCID 68107961, compound

Participants

Reaction Conditions

Reaction Steps

Benzyl 2-allyl-3-hydroxy-4-nitro-benzoate 29c (1.36 g, 4.30 mmol) was dissolved in 100 mL of 1,2-dichloroethane followed by the addition of m-chloroperbenzoic acid (1.18 g, 4.77 mmol). The reaction solution was heated to 70° C. and stirred for 3 hours. The resulting solution was cooled down to room temperature, added with 20 mL of saturated sodium thiosulfate solution, stirred for 30 minutes and extracted with ethyl acetate (20 mL×3). The combined organic phase was washed with water (20 mL), saturated sodium chloride solution (20 mL) successively, then dried over anhydrous magnesium sulfate, filtered and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain the title compound benzyl 2-(hydroxymethyl)-7-nitro-2,3-dihydrobenzofuran-4-carboxylate 29d (430 mg, yield: 30.1%) as a light yellow solid.

Provenance & Evidence