반응 #40656

반응 방정식

(S)-1-oxiranylmethanol

phthalimide

triphenylphosphine

diethyl azodicarboxylate

→

desired product

수율 73.9%

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

수율 73.9%

용매

tetrahydrofuran

반응 조건

후처리

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

실험 절차

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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