Diethyl Ether → 4-(4-Chlorophenyl)-2-pyridin-4-yl-4,5,6,7-tetrahydro-1-benzothiophene-4-ol

Participants

Reaction Steps

In a 250 mL round bottomed flask was placed 2-pyridin-4-yl-6,7-dihydro-1-benzothiophen-4(5H)-one (1400 mg, 6.1 mmol) and then dissolved in tetrahydrofuran (50 mL). To the mixture was added 1 M of 4-chlorophenylmagnesium bromide in ether (10 mL, 10 mmol) and the mixture was stirred for 1.5 h at rt. To the mixture were added a 5% aqueous solution of NH4Cl (100 mL) and EtOAc (100 mL). The resulting bi-phasic mixture was vigorously stirred for 15 min and then the aqueous phase was discarded. The organic phase was washed with brine (50 mL), and then 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 (40 g) column chromatography eluted with a 20% to 80% EtOAc/hexane to obtain 4-(4-chlorophenyl)-2-pyridin-4-yl-4,5,6,7-tetrahydro-1-benzothiophene-4-ol (2.9 g) as a colorless foam.

Provenance & Evidence