Sodium Azide → 11-Azidoundecan-1-ol
Reaction equation
Br[CH:2]([OH:13])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[N-:14]=[N+:15]=[N-:16].[Na+]>CN(C=O)C>[N:14]([CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][OH:13])=[N+:15]=[N-:16]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a 250 mL round-bottom dry flask was added anhydrous DMF (60 mL), 11 bromo-1-undecanol (10 g, 39.8 mmol) and NaN3 (2.85 g, 43.8 mmol). The solution was stirred with a magnetic bar for 24 hours at ambient temperature and quenched with DI water (60 mL). The solution was extracted with CH2Cl2 (3×40 mL), re-extracted with DI water (2×50 mL), dried with sodium sulfate overnight, and filtered. After the removal of the solvent by a rotoevaporator, a clear, colorless liquid (9.1 g, 93.4%) was obtained.