Hydrogen Peroxide → HCID 10681490, compound

Participants

Reaction Steps

LDH-PdOsW (0.4 g, 0.1 mmol), 4-iodoanisole (10 mmol), ethyl acrylate (10 mmol) and Et3N (11 mmol) were stirred at 70° C. for 16 h under nitrogen atmosphere. After completion of the Heck coupling, the heating was stopped and the reaction was allowed to reach room temperature. A mixture of (DHQ)2PHAL (7.8 mg, 0.1 mmol) and NMM (0.5 g, 5 mmol) in BuOH—H2O (5:1, 50 mL) was added in one portion to the reaction flask under stirring. H2O2 (30% aqueous, 15 mmol) was then slowly added over 15 h using a syringe pump. After the addition was complete, the stirring was continued for an additional 1 h and the catalyst was filtered and washed with ethyl acetate (100 mL). After removal of the solvent, thus obtained crude material was chromatographed on silica gel using hexane/ethyl acetate (1:1) as eluant to afford ethyl (2R,3S)-2,3-dihydroxy-3-(4-methoxyphenyl)propionate (92% yield).

Provenance & Evidence