反应详情

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 boron trifluoride 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.

1. washthe organic phase was washed with water (3×10 ml)
2. dry with materialdried (MgSO4)
3. customthe solvent was removed by evaporation
4. customThe crude was purified by preparative HPLC (
5. concentrationthe acetonitrile concentration
6. temperaturewas increased to 100%
7. additiona 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))
8. additionThe product containing fractions
9. customthe acetonitrile was removed by evaporation
10. additionEtOAc (10 ml) was added
11. washthe organic phase was washed with two portions of brine
12. dry with materialdried (MgSO4)
13. customAfter removing the solvent