Réaction #617061

Équation de réaction

3-furan methanol

diphenyl phosphoryl azide

undec-7-ene

→

3-azidomethyl furan

Rendement 95.0%

Solvants

toluene

Conditions de réaction

Traitement

1. 1
   AutreTo 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
   Lavagethe reaction mixture is washed with water (2×20 mL)
5. 5
   AutreVolatiles are evaporated under reduced pressure
6. 6
   AutreThe resulting residue is then purified by column chromatography (1:9 ethyl acetate/hexane)

Mode opératoire

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.

Source