反応 #643835

反応方程式

cyclopenteneoxide

NaN3

NH4Cl

→

desired product

収率 93.0%

trans-2-azido-cyclopentanol

収率 93.0%

溶媒

CH3OH

H2O

反応条件

後処理

1. 1
   温度The resulting mixture was heated to solvent
2. 2
   温度reflux for 18 h
3. 3
   温度then cooled to 23°
4. 4
   濃縮The mixture was concentrated
5. 5
   workup.ADDITIONthe residue was diluted with EtOAc
6. 6
   洗浄washed with H2O
7. 7
   乾燥the organic layer was dried over Na2SO4
8. 8
   濃縮concentrated

実験手順

To a soln of cyclopenteneoxide (2.0 g, 23.8 mmol) in CH3OH and H2O (40 mL) (4/1, v/v), were added NaN3 (7.73 g, 119 mmol) and NH4Cl (3.17 g, 59.2 mmol). The resulting mixture was heated to solvent reflux for 18 h then cooled to 23°. The mixture was concentrated and the residue was diluted with EtOAc, washed with H2O, the organic layer was dried over Na2SO4, concentrated to give the desired product (2.8 g, 93%). 1H NMR (CDCl3): δ 4.10 (m, 1H), 3.72 (m, 1H), 2.10 (m, 2H), 1.72-1.60 (m, 4H).

出典