تفاعل #40656

معادلة التفاعل

(S)-1-oxiranylmethanol

phthalimide

triphenylphosphine

diethyl azodicarboxylate

→

desired product

المردود 73.9%

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

المردود 73.9%

المذيبات

tetrahydrofuran

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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).

المصدر