Sodium Iodide → 3-Nitrophenethyl azide

To a solution of 3-nitrophenethyl alcohol (2 g, 11.97 mmol), Et3N (3.0 mL, 20.8 mmol) in CH2Cl2 (40 mL) is added methanesulfonyl chloride (1.0 mL, 12.9 mmol) at 0° C. After stirring for 0.5 hr, more CH2Cl2 is added. The solution is washed with water and brine, dried over Na2SO4 and concentrated. The residue is dissolved in DMF (30 mL), sodium azide (0.8 g,12.3 mmol), lithium chloride (0.53 g, 12.5 mmol) and catalytic amount of sodium iodide are added. The mixture is stirred at room temperature overnight. Most of DMF is then removed under vacuum and the residue is washed with water and brine, dried over Na2SO4 and concentrated. The residue is chromatographed over silica gel (eluent: hexane:ethyl acetate v/v 4:1) to give a pale yellow oil (1.8 g) as desired product.

1. washThe solution is washed with water and brine
2. dry with materialdried over Na2SO4
3. concentrationconcentrated
4. dissolutionThe residue is dissolved in DMF (30 mL)
5. stirringThe mixture is stirred at room temperature overnight
6. customMost of DMF is then removed under vacuum
7. washthe residue is washed with water and brine
8. dry with materialdried over Na2SO4
9. concentrationconcentrated
10. customThe residue is chromatographed over silica gel (eluent: hexane:ethyl acetate v/v 4:1)

ORD 기록

ord-64865ea286554bd8a1c116370d10d7b2

출처 데이터셋

uspto-grants-2001_09

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US06294529B1