Reacción #312593

Ecuación de reacción

diethyl azodicarboxylate

17

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

triphenylphosphine

phthalimide

→

desired product

Rendimiento 92.3%

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

Rendimiento 92.3%

Disolventes

THF

THF

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

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).

Fuente