Sodium Hydroxide → HCID 20206318, compound

A solution of ethyl 2-azidopentanoate (3.082 g, 18.0 mmol) in a mixture of methanol (10 ml) and water (5 ml) was treated dropwise with 20 ml of 1M sodium hydroxide (20 mmol, 1.1 equiv). After 1.5 h at room temperature, the methanol was evaporated under reduced pressure and the remaining aqueous phase was washed with ether (2×10 ml) and acidified with dilute HCl (3N) at 0° C. The aqueous phase was extracted with dichloromethane (3×25 ml). The combined organic phases were washed with water and dried over anhydrous sodium sulfate. Evaporation of the solvent gave an oil which was distilled (bulb to bulb) to give 2.393 g (93%) of a clear liquid: 80°-85° C./0.5 toor (air bath temperature; ir (firm) νmax : 2110 (N3), 1720 cm-1 (C=O); 1Hmr (CDCl3) δ: 3.90 (1H, dd, J= 6, J=7, H-2), 2.0-1.0 (4H, m, H-3, H-4) and 1.00 ppm (3H, distorted t, J=6, H-5); Anal. calcd for C5H9N3O2 : C 41.95, H 6.34, N 29.36; found: C 42.06, H 6.49, N 29.26.

1. customthe methanol was evaporated under reduced pressure
2. washthe remaining aqueous phase was washed with ether (2×10 ml)
3. customacidified with dilute HCl (3N) at 0° C
4. extractionThe aqueous phase was extracted with dichloromethane (3×25 ml)
5. washThe combined organic phases were washed with water
6. dry with materialdried over anhydrous sodium sulfate
7. customEvaporation of the solvent
8. customgave an oil which
9. distillationwas distilled (bulb to bulb)

ORD record

ord-6c7727172141485987f66f592530f064

Source dataset

uspto-grants-1983_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04378314