3-Furanmethanol → 3-(Azidomethyl)furan

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.

1. customTo a 50 mL round-bottomed flask equipped with a magnetic stirbar
2. additionwas added dropwise
3. waitAfter this period
4. washthe reaction mixture is washed with water (2×20 mL)
5. customVolatiles are evaporated under reduced pressure
6. customThe resulting residue is then purified by column chromatography (1:9 ethyl acetate/hexane)

ORD-Eintrag

ord-c3fe0b6b29dc43f7b95965d9f59d874e

Quelldatensatz

uspto-grants-2013_02

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08367713B2