Sodium Azide → HCID 20505601, compound

Participants

Reaction Steps

t-Butyl 3-tosyloxypentanoate (7.75 g, 23.6 mmol) was added to a suspension of sodium azide (3.07 g, 47.2 mmol) in dry DMSO (135 ml) and stirred at room temperature for 66 h. The reaction mixture was poured into ice-water (200 ml) and extracted with CH2Cl2 (2×150 ml). The organic extracts were combined, washed with water (4×150 ml) and dried over anhydrous MgSO4. Evaporation of the CH2Cl2 under reduced pressure gave an oil (4.18 g, 89.4%). ir (neat) νmax : 2096 (N3) and 1720 cm-1 (C=O of ester); 1Hmr (CDCl3) δ: 1.0 (3H, t), 1.27-1.85 (2H, m), 1.48 (9H, s), 2.40 (2H, d) and 3.68 ppm (H, m).

Provenance & Evidence