Cesium carbonate → 6-(4-Methanesulfonyl-phenoxy)-2-methyl-2,3-dihydro-benzofuran-4-carboxylic acid methyl ester

Participants

Reaction Conditions

Reaction Steps

4-Fluorophenyl methyl sulfone (307 mg, 1.76 mmol) and Cs2CO3 (1.15 g, 3.52 mmol) were added to a solution of 6-hydroxy-2-methyl-2,3-dihydro-benzofuran-4-carboxylic acid methyl ester (1e) (366 mg, 1.76 mmol) in DMF (8 mL). The mixture was heated to 120° C. for 1 hr, cooled to room temperature, quenched with H2O (50 mL) and extracted with EtOAc (2×50 mL). The organic layers were washed with H2O (2×80 mL), dried over MgSO4 and concentrated. The residue was purified by flash column chromatography eluting with 40% EtOAc in hexanes to give a pale brown solid (350 mg, 55% yield). 1H NMR (400 MHz, CDCl3) δ 7.84-7.93 (m, 2 H) 7.18 (d, J=2.02 Hz, 1 H) 7.04-7.14 (m, 2 H) 6.67 (d, J=2.27 Hz, 1 H) 4.94-5.17 (m, 1 H) 3.89 (s, 3 H) 3.68 (dd, J=17.43, 8.84 Hz, 1 H) 3.13 (dd, J=17.43, 7.58 Hz, 1 H) 3.07 (s, 3 H) 1.51 (d, J=6.32 Hz, 3 H);); LCMS for C18H18O6S m/z 363.0 (M+H)+.

Provenance & Evidence