Sodium Azide → HCID 19390014, compound

Participants

Reaction Steps

A solution of 0.12 g of 9-(oxiranylmethoxy)-3-(2-(3-furyl)ethyl)-spiro[5.5]-undecane (prepared as intermediate in Ex. 21), 0.130 g of sodium azide and 0.030 g of tetrabutylammonium hydrogen sulfate in 1.5 ml of water and 1.5 ml of benzene was vigorously stirred at reflux temperature for 48 hrs. The reaction mixture was then cooled to room temperature, diluted with ethyl acetate, the organic phase washed with water several times, dried on sodium sulfate and evaporated to dryness. The residue was purified by chromatography (SiO2 ; n-hexane/diethylether 50/50), to give 0.110 g of 9-(2-azido-3-hydroxypropoxy)-3-(2-(3-furyl)ethyl)-spiro[5.5]-undecane as brown foam. [TLC: Rf=0.48 (SiO2 plates, diethylether/n-hexane 70/30). PG,28 1H-NMR (300 MHz, CDCl3, ppm from TMS): 7.35 (1H, m), 7.20 (1H, m), 6.23 (1H, m), 4.00-3.80 (1H, m), 3.55-3.20 (5H, m), 2.42 (2H, t), 1.90-0.80 (19H, m)].

Provenance & Evidence