Sodium Chloride → HCID 10635673, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 42.94 g (108 mmol) of the tosylate (4) in 250 ml of DMF (N,N-dimethylformamide) was added 31.52 g (485 mmol) of sodium azide. The solution was heated under argon for 4 hours at 80° C. The reaction mixture was cooled and poured into 600 ml of saturated NaCl, and the resulting oil was separated. The aqueous solution was extracted three times with Et2O. The Et2O extracts were combined with the oil and washed once with saturated NaCl, dried (MgSO4), and concentrated, yielding 33.0 g of the azide (5) as a crude product that was sufficiently pure to use in the next step (f). An analytical sample of the azide (5) was obtained by flash chromatography on silica gel, eluting CH2Cl2 -EtOAc (20:1) to produce a colorless oil.

Provenance & Evidence