反应详情

Diethylazodicarboxylate (0.77 g, 3.8 mmol) was added to solution of 3-bromophenol (0.50 g, 3.2 mmol), 3-bromopropanol (0.53 g, 3.8 mmol), triphenylphosphine (1.0 g, 3.8 mmol) and THF (10 mL). The solution was maintained at RT for 16 h and then concentrated in vacuo. The residue was partitioned between methylene chloride and 10% NaHCO3 aq. solution and layers separated. The aqueous layer was extracted with methylene chloride (2×10 mL). The organic layers were combined, dried (MgSO4) and concentrated in vacuo. The crude product was purified by flash column chromatography (100 g silica gel 60, 230-400 mesh, 9:1 hexane:ethyl acetate as eluent) to give 0.63 g (71%) of the title compound as a pale yellow liquid. MS (ESI) 293.0 [M+H]+.

1. concentrationconcentrated in vacuo
2. customThe residue was partitioned between methylene chloride and 10% NaHCO3 aq. solution and layers
3. customseparated
4. extractionThe aqueous layer was extracted with methylene chloride (2×10 mL)
5. dry with materialdried (MgSO4)
6. concentrationconcentrated in vacuo
7. customThe crude product was purified by flash column chromatography (100 g silica gel 60, 230-400 mesh, 9:1 hexane:ethyl acetate as eluent)