Tert-butyl acetoacetate → tert-butyl 2-hydroxyimino-3-oxobutanoate

HRID 1937530Notes

Reaction equation

HRID 1937530 reaction equation
[C:1]([O:5][C:6](=[O:11])[CH2:7][C:8](=[O:10])[CH3:9])([CH3:4])([CH3:3])[CH3:2].[N:12]([O-])=[O:13].[Na+]>C(O)(=O)C>[C:1]([O:5][C:6](=[O:11])[C:7](=[N:12][OH:13])[C:8](=[O:10])[CH3:9])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 15538Tert-butyl acetoacetateHCID 23668193Sodium Nitrite

Product 1

HCID 178468384tert-butyl 2-hydroxyimino-3-oxobutanoate

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
10 °C

Procedure

t-Butyl-3-oxobutyrate (158 g, 1 mol) was dissolved in 200 mL of acetic acid in a 500 mL 3-neck round bottom flask equipped with a thermometer, addition funnel and mechanical stirring. The mixture was cooled in an ice bath to about 10° C. Sodium nitrite (69 g, 1 mol) was added over 75 minutes keeping the temperature under 15° C. The cold bath was removed and the mixture stirred for 30 minutes and then allowed to stand for 3.5 hours to give t-butyl-2-hydroximino-3-oxobutyrate.

Workup

  1. customequipped with a thermometer, addition funnel and mechanical stirring
  2. customunder 15° C
  3. customThe cold bath was removed
  4. waitto stand for 3.5 hours

Sources & evidence

ORD record
ord-f8080791f5624585bf7458f35bbc5345
Source dataset
uspto-grants-2002_05
Patent number
US06395734B1

Reaction notes

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