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) was added methanesulfonyl chloride (1.0 mL, 12.9 mmol) at 0° C. After stirring for 0.5 hr, more CH2Cl2 was added. The solution was washed with water and brine, dried over Na2SO4 and concentrated. The residue was 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 were added. The mixture was stirred at room temperature overnight. Most of DMF was then removed under vacuum and the residue was washed with water and brine, dried over Na2SO4 and concentrated. The residue was 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 was washed with water and brine
2. dry with materialdried over Na2SO4
3. concentrationconcentrated
4. dissolutionThe residue was dissolved in DMF (30 mL)
5. stirringThe mixture was stirred at room temperature overnight
6. customMost of DMF was then removed under vacuum
7. washthe residue was washed with water and brine
8. dry with materialdried over Na2SO4
9. concentrationconcentrated
10. customThe residue was chromatographed over silica gel (eluent: hexane:ethyl acetate v/v 4:1)

ORD-Eintrag

ord-faf6a144ef334aa9b1937ad79b9ec00c

Quelldatensatz

uspto-grants-2002_06

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06399597B1