Sodium Azide → Methyl 11-azidoundecanoate

Participants

Reaction Conditions

Reaction Steps

Sodium azide (4.66 g, 72 mmol) and tetrabutylammonium iodide (66 mg, 0.18 mmol) were successively added to a solution of methyl 11-bromoundecanoate (commercially available at Aldrich, 5.00 g, 17.9 mmol) in N,N-dimethylformamide (50 ml). The reaction mixture was heated to 60° C. for 16 h and cooled to room temperature. It was diluted with water (200 ml) and extracted with ethyl acetate (200 ml). The aqueous phase was washed with water (2×200 ml). The organic phase was dried over sodium sulphate. The solvent was removed in vacuo to give 4.28 g of methyl 11-azidoundecanoate.

Provenance & Evidence