反応 #312593

反応方程式

diethyl azodicarboxylate

17

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

triphenylphosphine

phthalimide

→

desired product

収率 92.3%

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

収率 92.3%

溶媒

THF

THF

反応条件

後処理

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

実験手順

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).

出典