Reacción #40656

Ecuación de reacción

(S)-1-oxiranylmethanol

phthalimide

triphenylphosphine

diethyl azodicarboxylate

→

desired product

Rendimiento 73.9%

(S)-2-oxiranylmethylisoindole-1,3-dione

Rendimiento 73.9%

Disolventes

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   ConcentraciónThe mixture was concentrated under vacuum
2. 2
   Otrothe oily residue was purified by flash silica column chromatography

Procedimiento

To a cold solution of (S)-1-oxiranylmethanol (5 g, 67.5 mmol) and phthalimide (9.9 g, 67.3 mmol) in tetrahydrofuran (200 mL) in ice bath was added triphenylphosphine (17.9 g, 68.2 mmol) and diethyl azodicarboxylate (12.3 g, 70.6 mmol). The mixture was stirred at 0° C. for 2 h and at ambient temperature for 48 h. The mixture was concentrated under vacuum, and the oily residue was purified by flash silica column chromatography, yielding the desired product (10.1 g) as pale yellow solid: Rf=0.51 in 1:1 EtOAc/hexane. 1H—NMR (CDCl3, 300 MHz): δ (ppm) 7.76-7.64 (m, 2H), 7.63-7.60 (m, 2H), 3.9-3.8 (dd, 1H), 3.70-3.65 (dd, 1H), 3.15 (m, 1H), 2.70-2.67 (dd, 1H), 2.58-2.55 (dd, 1H).

Fuente