反应详情

温度

55 °C

Methyl 2-{[4-(2-hydroxyethyl)phenoxy]methyl}benzoate (1 g, 3.49 mmol), 4-(benzyloxy)phenol (0.7 g, 3.49 mmol) and triphenylphosphine (1.01 g, 3.84 mmol) was added to a dry round bottomed flask fitted with a septum. N2 was flushed through the flask for 5 minutes followed by the addition of dry toluene (30 ml) and diisopropylazo-dicarboxylate (0.78 g, 3.84 mmol). The reaction mixture was stirred at 55° C. overnight. The solvent was removed by evaporation and the crude material 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, 0.7 g of methyl 2-[(4-{2-[4-(benzyloxy)phenoxy]ethyl}phenoxy)methyl]benzoate was isolated (yield 42.8%).

1. customfitted with a septum
2. customN2 was flushed through the flask for 5 minutes
3. customThe solvent was removed by evaporation
4. customthe crude material 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
14. customby evaporation