Reaktion #617061

Reaktionsgleichung

3-furan methanol

diphenyl phosphoryl azide

undec-7-ene

→

3-azidomethyl furan

Ausbeute 95.0%

Lösungsmittel

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeTo a 50 mL round-bottomed flask equipped with a magnetic stirbar
2. 2
   workup.ADDITIONwas added dropwise
3. 3
   workup.WAITAfter this period
4. 4
   Waschenthe reaction mixture is washed with water (2×20 mL)
5. 5
   SonstigeVolatiles are evaporated under reduced pressure
6. 6
   SonstigeThe resulting residue is then purified by column chromatography (1:9 ethyl acetate/hexane)

Vorschrift

To a 50 mL round-bottomed flask equipped with a magnetic stirbar was added 3-furan methanol (1.00 g, 10.2 mmol) and a solution of diphenyl phosphoryl azide (3.37 g, 12.2 mmol) in toluene (30 mL). The stirring solution is allowed to cool to 0° C., in which 1, 8 Diazabycyclo [5.4.0.]undec-7-ene (1.86 g, 12.2 mmol) was added dropwise. The reaction is allowed to slowly warm to ambient temperature for an additional 16 hours of stirring. After this period, the reaction mixture is washed with water (2×20 mL) and then with 5% HCl (20 mL). Volatiles are evaporated under reduced pressure. The resulting residue is then purified by column chromatography (1:9 ethyl acetate/hexane) providing 3-azidomethyl furan (1.19 g, 95%) as a colorless oil. 1H NMR (400 MHz, CDCl3) δ 7.46 (d, 1H), δ 7.44 (s, 1H), δ 6.42 (d, 1H), δ 4.20 (s, 2H). ppm; 13C NMR (75 MHz, CDCl3) δ 144.1, 141.1, 110.4, 92.1, 45.8 ppm; LRMS (EI) calcd for C5H5N3O (M+) 123. found 123.

Quelle