تفاعل #617061

معادلة التفاعل

3-furan methanol

diphenyl phosphoryl azide

undec-7-ene

→

3-azidomethyl furan

المردود 95.0%

المذيبات

toluene

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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.

المصدر