Potassium Carbonate → [(2R)-7-(Methylsulfonyl)-2,3-dihydro-1,4-benzodioxin-2-YL]methanol

Beteiligte Stoffe

Reaktionsschritte

Two batches of [(2R)-7-bromo-2,3-dihydro-1,4-benzodioxin-2-yl]methanol (2.2 g, 8.9 mmol), sodium methanesulfinate (85%) (1.6 g, 13.3 mmol), CuI (0.2 g, 0.9 mmol), L-proline (0.2 g, 1.8 mmol) and K2CO3 (0.2 g, 1.8 mmol) in DMSO (20 ml) were heated under microwave radiation at 140° C. for 3 h in nitrogen-flushed vials. Water and EtOAc were added. The water layer was extracted with EtOAc (3×100 ml) and the combined organic phases were washed with LiCl (5%), HCl (1 N) and brine. The resulting solution was dried (Na2SO4) and evaporated to dryness. The residue was purified by flash column chromatography (isooctane/EtOAc) to give the title compound (1.7 g). MS m/z (rel. intensity, 70 eV) 244 (M+, bp), 213 (39), 165 (26), 134 (22), 79 (23).

Herkunft & Nachweise