反应详情

Methyl 2-[(4-{3-[4-(benzyloxy)phenoxy]propyl}phenoxy)methyl]benzoate (0.047 g, 0.097 mmol) was dissolved in a mixture of THF/water (7/1, 2 ml) and lithium hydroxide (9.3 mg, 0.39 mmol) was added. The reaction was performed in a single node microwave oven (7 min, 150° C.). The reaction mixture was acidified (HCl, 1 M, 1 ml) and the water phase was washed with two portions of EtOAc (2×5 ml). The organic phases were combined, dried (MgSO4) and the solvent was removed by evaporation. The crude product 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). Removing the solvent by evaporation gave 2 mg of 2-[(4{3-[4-(benzyloxy)phenoxy]propyl}phenoxy)methyl]-benzoic acid (yield 4.4%).

1. additionwas added
2. customThe reaction was performed in a single node microwave oven
3. custom(7 min, 150° C.)
4. washthe water phase was washed with two portions of EtOAc (2×5 ml)
5. dry with materialdried (MgSO4)
6. customthe solvent was removed by evaporation
7. customThe crude product was purified by preparative HPLC (
8. concentrationthe acetonitrile concentration
9. temperaturewas increased to 100%
10. 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))
11. additionThe product containing fractions
12. customthe acetonitrile was removed by evaporation
13. additionEtOAc (10 ml) was added
14. washthe organic phase was washed with two portions of brine
15. dry with materialdried (MgSO4)
16. customRemoving the solvent
17. customby evaporation