Sodium Azide → Acetic acid 3-azido-propyl ester

Participants

Reaction Conditions

Reaction Steps

A solution of 3-bromopropyl acetate (1.0 g, 6.0 mmol) in water (10 mL) was added to sodium azide (780 mg, 12.1 mmol). The solution was stirred at 90° C. overnight. The solution was extracted three times with 15 mL CH2Cl2 and dried with MgSO4. Solvent was removed under reduced pressure to afford 3-azidopropyl acetate as a pale yellow oil. A solution of tripropargylamine (12.3 mg, 0.941 mmol) in tetrahydrofuran (6.5 mL) was added to 3-azidopropyl acetate (0.672 g, 4.71 mmol) and Cu(I) acetate (5.8 mg, 5 mol %). The solution was refluxed overnight under inert atmosphere. Solvent was removed under reduced pressure. Silica chromatography purification (Rf=0.5, 5-10% MeOH in CH2Cl2) afforded acetyl-protected THPTA as a yellow oil.

Provenance & Evidence