Tert-butyl acetoacetate → 1-tert-Butoxy-2-diazonio-3-oxobut-1-en-1-olate

HRID 453283Notes

Reaction equation

HRID 453283 reaction equation
C(NC1C=CC(S([N:14]=[N+:15]=[N-])(=O)=O)=CC=1)(=O)C.[O:17]=[C:18]([CH3:27])[CH2:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21]>CC#N>[N+:14](=[C:19]([C:18](=[O:17])[CH3:27])[C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])=[N-:15]

Participants

4

Reactant 2

HCID 15538Tert-butyl acetoacetateHCID 51291854-Acetamidobenzenesulfonyl azide

Product 1

HCID 538143121-tert-Butoxy-2-diazonio-3-oxobut-1-en-1-olateYield 77%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4-acetamidobenzenesulfonyl azide (1.5 ml) was added to a solution of tert-butyl 3-oxobutanoate (1.86 g, 10.12 mmol) and TEA (3.85 ml) in CH3CN (60 ml). The mixture was stirred at room temperature overnight, concentrated and purified by flash chromatography to give tert-butyl 2-diazo-3-oxobutanoate as a yellow liquid (1.3 g, 77% yield).

Workup

  1. concentrationconcentrated
  2. custompurified by flash chromatography

Sources & evidence

ORD record
ord-a419e9277746484f87eb68f3669f41e6
Source dataset
uspto-grants-2013_07
Patent number
US08492401B2

Reaction notes

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