Dimethyl Sulfide → Methyl 2-({4-[3-(4-hydroxyphenoxy)propyl]phenoxy}methyl)benzoate

Participants

Reaction Steps

Methyl 2-[(4-{3-[4(benzyloxy)phenoxy]propyl}phenoxy)methyl]benzoate (0.70 g, 1.45 mmol) was dissolved in dichloromethane (10 ml). Dimethylsulfide (1.08 g, 17.4 mmol) and borontrifluoride etherate (2.06 g, 14.5 mmol) was added and the mixture was stirred at room temperature for six hours. EtOAc (10 ml) was added and the organic phase was washed with water (3×10 ml), dried (MgSO4) and the solvent was removed by evaporation. The crude was purified by preparative HPLC (started with acetonitrile/buffer 60/40 and then the acetonitrile concentration was increased to 100%, the buffer was a mixture of acetonitrile/water 10/90 and ammonium acetate (0.1 M, column KR-100-7-C8, 50 mm×250 mm, flow 40 ml/min)). The product containing fractions were pooled and the acetonitrile was removed by evaporation. EtOAc (10 ml) was added and the organic phase was washed with two portions of brine and dried (MgSO4). After removing the solvent by evaporation 0.328 gram of methyl 2-({4-[3-(4-hydroxyphenoxy)propyl]-phenoxy}methyl)benzoate (yield 57.6%) was obtained.

Provenance & Evidence