反应 #312593

反应方程式

diethyl azodicarboxylate

17

4-[(2-Phenyl)-1,3-dioxolan-4-yl]-1-butanol

triphenylphosphine

phthalimide

→

desired product

收率 92.3%

2-Phenyl-4-(4-phtalimidobut-1-yl)-1,3-dioxolane

收率 92.3%

溶剂

THF

THF

反应条件

后处理

1. 1
   浓缩the solution was concentrated
2. 2
   其他the residue was triturated with ether (˜150 mL)
3. 3
   其他to precipitate triphenylphosphine oxide which
4. 4
   其他was then removed by filtration
5. 5
   浓缩The filtrate was concentrated
6. 6
   其他to give an oily residue which
7. 7
   其他was chromatographed on silica eluting with 33% ethyl acetate in hexane
8. 8
   其他by drying under vacuum

实验过程

A solution of diethyl azodicarboxylate (8.6 g, 49.4 mmol) in 40 mL of THF was slowly added to a cold (ice bath) solution of 17 (10.0 g, 45.0 mmol), triphenylphosphine (13.0 g, 49.5 mmol) and phthalimide (7.3 g, 49.7 mmol) in 60 mL of THF. After being kept at ambient temperature overnight, the solution was concentrated and the residue was triturated with ether (˜150 mL) to precipitate triphenylphosphine oxide which was then removed by filtration. The filtrate was concentrated to give an oily residue which was chromatographed on silica eluting with 33% ethyl acetate in hexane. Concentration of the pure product fractions followed by drying under vacuum afforded 14.6 g (92%) of the desired product as a semi-solid (a mixture of diastereomers): 1H NMR (CDCl3, 300 MHz, ppm) 7.85 (m, 2H), 7.71 (m, 2H), 7.46 (m, 2H), 7.36 (m, 3H), 5.90 (s, 0.4H), 5.78 (s, 0.6H), 4.3-4.0 (m, 2H), 3.68 (m, 3H), 1.9-1.3 (m, 6H).

来源