Dimethylformamide → 2-(2-(2-Azidoethoxy)ethoxy)ethanol
Reaction equation
[C:1]([CH2:5][O:6][C:7]1[CH:12]=CC(N=NC2C=CC(CO)=CC=2)=CC=1)([O:3][CH3:4])=O.[N-:23]=[N+:24]=[N-:25].[Na+].CN([CH:30]=[O:31])C>>[N:23]([CH2:12][CH2:7][O:6][CH2:5][CH2:1][O:3][CH2:4][CH2:30][OH:31])=[N+:24]=[N-:25]Participants
4
Conditions
- Temperature
- 80 °C
Procedure
Compound 3 (10.0 g, 59.50 mmol) was dissolved in anhydrous DMF (200 mL), to which NaN3 (77.3 g, 119.00 mmol) was added and reaction mixture stirred at 80° C. or 48 hours. Solvents were removed under reduced pressure and residue dissolved in DCM (200 mL), washed with water (400 mL) and brine (100 mL) before being dried over Na2SO4. Solvent was evaporated under reduced pressures and residue purified by silica gel column chromatography using EA:hexane (6:4) to obtain 4 as a liquid (7.80 g, 75% yield). 1H-NMR (500 MHz, CDCl3): δ 2.34 (d, 1H, J=5.5 Hz, OH), 3.93 (t, 2H, J=6.0 Hz, Ha), 3.61 (t, 2H, J=4.5 Hz, Hb), 3.65-3.68 (m, 6H, Hc, He, Hf), 3.73 (q, 2H, J=5.5 Hz, Hd); 13C-NMR (125 MHz, CDCl3): δ 50.62 (Ca), 61.73 (Cf), 70.02 (Cb), 70.36 (Ce), 70.63 (Cc), 72.45 (Cd). EI-MS: [M+Na]+ C6H13N3NaO3 calcd 198.08, obsd 198.07