Реакция #40656

Уравнение реакции

(S)-1-oxiranylmethanol

phthalimide

triphenylphosphine

diethyl azodicarboxylate

→

desired product

Выход 73.9%

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

Выход 73.9%

Растворители

tetrahydrofuran

Условия реакции

Обработка

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

Методика

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).

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