Diethyl Ether → HCID 68183080, compound

Participants

Reaction Steps

In a 100 mL round bottomed flask was placed 5,5-dimethyl-2-pyridin-4-yl-6,7-dihydro-1-benzothiophen-4(5H)-one (380 mg, 1.5 mmol) and then dissolved in tetrahydrofuran (30 mL). To the mixture was added 1 M of 4-chlorophenyl magnesiumbromide in ether (3.5 mL, 3.5 mmol) and then stirred for 3 h at rt. To the mixture was added 1 M of 4-chlorophenyl magnesiumbromide in ether (2.5 mL, 2.5 mmol) and then stirred for 16 h at rt. The mixture was stirred for 10 h at 70° C. The mixture was allowed to cool to rt and then 1 M of 4-chlorophenyl magnesiumbromide in ether (5 mL, 5 mmol) was added and the mixture was stirred for 16 h at rt. The mixture was diluted with saturated aqueous solution of NH4Cl (50 mL), which was extracted with EtOAc (50 mL×2). The combined organic phase was dried over anhydrous MgSO4. Insoluble materials were removed by filtration and the filtrate was concentrated under reduced pressure. The residue was purified by pre-packed silica gel (24 g) column chromatography eluted with a 30% to 100% EtOAc/hexane to obtain title compound (530 mg; 97%) as a colorless foam. LCMS: (FA) ES+ 370, 372; 1H NMR (400 MHz, d6-DMSO) δ ppm 8.48 (dd, 2H), 7.45 (dd, 2H), 7.33 (d, 2H), 7.23-7.25 (m, 2H), 5.55 (s, 1H), 2.87-2.91 (m, 2H), 1.84-1.90 (m, 1H), 1.57-1.63 (m, 1H, 0.95 (s, 3H), 0.62 (s, 3H).

Provenance & Evidence