Sodium hydride → Ethyl 4-(2-azidopropoxy)-3-oxobutanoate

HRID 1589652Notes

Reaction equation

HRID 1589652 reaction equation
[N:1]([CH:4]([CH3:7])[CH2:5][OH:6])=[N+:2]=[N-:3].[H-].[Na+].Cl[CH2:11][C:12](=[O:19])[CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15]>O1CCCC1>[N:1]([CH:4]([CH3:7])[CH2:5][O:6][CH2:11][C:12](=[O:19])[CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[N+:2]=[N-:3]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 69484Ethyl 4-chloroacetoacetateHCID 216348092-Azidopropan-1-ol

Product 1

HCID 20245565Ethyl 4-(2-azidopropoxy)-3-oxobutanoateYield 87.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of the 2-azidopropan-1-ol (10.1 g) in tetrahydrofuran (100 ml) was added over two minutes to a stirred, ice-cooled suspension of sodium hydride (6.6 g; 80% dispersion in oil) in tetrahydrofuran (50 ml). The mixture was stirred for 15 minutes with ice-cooling and then treated over 20 minutes with a solution of ethyl 4-chloroacetoacetate (16.4 g) in tetrahydrofuran (150 ml). The mixture was stirred at room temperature for 16 hours and evaporated. The residue was diluted with water, washed twice with ether, acidified with 2M hydrochloric acid, and extracted three times into ether. The combined ether extracts were dried (Na2SO4) and evaporated to give crude ethyl 4-(2-azidoprop-1-oxy)acetoacetate (20 g), used directly.

Workup

  1. temperaturecooled
  2. temperaturecooling
  3. stirringThe mixture was stirred at room temperature for 16 hours
  4. customevaporated
  5. additionThe residue was diluted with water
  6. washwashed twice with ether
  7. extractionextracted three times into ether
  8. dry with materialThe combined ether extracts were dried (Na2SO4)
  9. customevaporated

Sources & evidence

ORD record
ord-800298da283243dcb9322a0bd834c7a1
Source dataset
uspto-grants-1986_02
Patent number
US04572909

Reaction notes

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