Potassium Hydroxide → 4-azidobutanoic Acid

HRID 2280972Notes

Reaction equation

HRID 2280972 reaction equation
[N:1]([CH2:4][CH2:5][CH2:6][C:7]([O:9]CC)=[O:8])=[N+:2]=[N-:3].[OH-].[K+]>CO.O>[N:1]([CH2:4][CH2:5][CH2:6][C:7]([OH:9])=[O:8])=[N+:2]=[N-:3]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 12382175Ethyl 4-azidobutanoate

Product 1

HCID 118047834-azidobutanoic AcidYield 92.4%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

Ethyl 4-bromobutanoate (17.11 g, 87.7 mmol) and NaN3 (28.50 g, 438.5 mmol) was dissolved in 70 mL DMF and reacted at 77° C. for 30 hours. 250 mL of 4:1 EtOAc/hexanes was added, and was washed twice with 250 mL saturated aqueous sodium bicarbonate, and once with 200 mL water. Organic layer was dried over sodium sulfate, filtered and concentrated in vacuo to give ethyl 4-azidobutanoate 6 (13.26 g, 96%). Ethyl 4-azidobutanoate 6 (6.18 g, 39.29 mmol) was then saponified using excess KOH in 12:10 methanol/water at 0° C. for 5 minutes and then ambient temperature for 11 hours, followed by acid workup to yield 4-Azidobutanoic acid 7 (4.69 g, 92%). 1H NMR (400 MHz, cdcl3) δ 1.71-1.98 (2H, m), 2.45 (2H, t, J=7.2 Hz), 3.35 (2H, t, J=6.7 Hz), 11.21 (1H, s) ppm.

Workup

  1. customat 0° C.
  2. customfor 5 minutes

Sources & evidence

ORD record
ord-0877ff2e22364d4c97c241e0ed7946f1
Source dataset
uspto-grants-2015_09
Patent number
US09139565B2

Reaction notes

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