Sodium Hydroxide → HCID 20206318, compound

HRID 1680344Notes

Reaction equation

HRID 1680344 reaction equation
C([O:3][C:4](=[O:12])[CH:5]([N:9]=[N+:10]=[N-:11])[CH2:6][CH2:7][CH3:8])C.[OH-].[Na+]>CO.O>[N:9]([CH:5]([CH2:6][CH2:7][CH3:8])[C:4]([OH:12])=[O:3])=[N+:10]=[N-:11]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 23448170HCID 23448170, compound

Product 1

HCID 20206318HCID 20206318, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

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 compound 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: bp 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.

Workup

  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 compound 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)

Sources & evidence

ORD record
ord-27e651ec648143d6b1d51c7c0bf5d129
Source dataset
uspto-grants-1981_06
Patent number
US04272437

Reaction notes

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