Reaktion #1555904

Reaktionsgleichung

oxime

1-Benzo[1,3]dioxol-5-yl-ethanone oxime

lithium aluminum hydride

di-iso-propyl amine

→

15

Ausbeute 88.7%

2-Benzo[1,3]dioxol-5-yl-aziridine

Ausbeute 88.7%

Lösungsmittel

tetrahydrofuran

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe emptied reaction vessel
2. 2
   Waschenwas rinsed with tetrahydrofuran (22 mL)
3. 3
   SonstigeThe reaction vessel was equipped with a reflux condenser under nitrogen atmosphere
4. 4
   TemperaturThe mixture was cooled to 25° C.
5. 5
   workup.ADDITIONdiluted with ice water (400 mL)
6. 6
   Extraktionthe product was extracted with dichloromethane (5×200 mL)
7. 7
   TrocknenThe combined organic layers were dried (sodium sulfate), gravity
8. 8
   Filtrationfiltered
9. 9
   Einengenconcentrated by rotary evaporation
10. 10
    SonstigeThe residue was purified by silica gel column chromatography (5% triethylamine in ethyl acetate)

Vorschrift

A solution of oxime 12 (2.7 g, 15 mmol, 1.0 equiv) in tetrahydrofuran (60 mL) at 25° C. was transferred via cannula to a stirred suspension of lithium aluminum hydride (3.5 g, 61 mmol, 4.0 equiv) and di-iso-propyl amine (8.5 mL, 61 mmol, 4.0 equiv) in tetrahydrofuran (70 mL) at 25° C. The emptied reaction vessel was rinsed with tetrahydrofuran (22 mL) and the resulting solution was also transferred via cannula. The reaction vessel was equipped with a reflux condenser under nitrogen atmosphere and heated to 60° C. via oil bath for 4 h. The mixture was cooled to 25° C., diluted with ice water (400 mL), and the product was extracted with dichloromethane (5×200 mL). The combined organic layers were dried (sodium sulfate), gravity filtered, and concentrated by rotary evaporation. The residue was purified by silica gel column chromatography (5% triethylamine in ethyl acetate) to afford 15 (2.17 g, 88% yield) as a pale yellow oil. Rf=0.40 (5% triethylamine in ethyl acetate); 1H NMR (500 MHz, CDCl3) δ 6.75 (br s, 2H, ArH), 6.70 (br s, 1H, ArH), 5.93 (s, 2H, OCH2O), 2.97 (br s, 1H, ArCH), 2.17 (br s, 1H, CH2), 1.67 (br s, 1H, CH2).

Quelle