Sodium Azide → (+/-)-1-Methoxy-2-butyl Azide
Reaction equation
CS(O[CH:6]([CH2:10][CH3:11])[CH2:7][O:8][CH3:9])(=O)=O.[N-:12]=[N+:13]=[N-:14].[Na+]>CN(C=O)C>[CH3:9][O:8][CH2:7][CH:6]([N:12]=[N+:13]=[N-:14])[CH2:10][CH3:11]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 57.5 °C
Procedure
A solution of crude mesylate 1 (90.0 g, 0.495 mol) in DMF (500 mL) was treated with NaN3 (48.22g, 0.74 mol, 1.5 equiv) at 25° C. under N2. The resulting reaction mixture was warmed to 55-60° C. for 6-8 h with stirring before being quenched with H2O (500 mL). The pale-yellow solution was then extracted with EtOAc or Et2O (4×200 mL). The combined EtOAc (or Et2O) extracts were washed with H2O (3×500 mL), dried (MgSO4), and concentrated in vacuo. The residual solution was found to contain desired azide 2 (60.3 g, 64.5 g theoretical, 94%), which was found to be pure enough and directly used in the following reaction without further purification.