Ethyl 3-oxovalerate → HCID 178472905, compound

HRID 619230Notes

Reaction equation

HRID 619230 reaction equation
[O:1]=[C:2]([CH2:9][CH3:10])[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].[N:11]([O-])=[O:12].[Na+]>C(O)(=O)C.O.CCOCC>[OH:12]/[N:11]=[C:3](/[C:2](=[O:1])[CH2:9][CH3:10])\[C:4]([O:6][CH2:7][CH3:8])=[O:5]

Participants

6

Reactant 2

HCID 78656Ethyl 3-oxovalerateHCID 23668193Sodium Nitrite2×

Product 1

HCID 178472905HCID 178472905, compoundYield 72.9%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

A solution of ethyl 3-oxopentanoate (50 g) in acetic acid (66 ml) was cooled to 0° C. and treated dropwise with 2/3 portion of a solution of sodium nitrite (52.6 g) in water (170 ml). After dropping (40 minutes), the reaction mixture was diluted with water (170 ml) and stirred for 1.5 hours. The mixture was treated with the residual solution of sodium nitrite at room temperature and stirred for more 1.5 hours. The reaction mixture was diluted with ether and quenched by aqueous sodium bicarbonate. The organic phase was washed with brine and dried with magnesium sulfate. The solvent was removed under reduced pressure to afford ethyl 2-(Z)-hydroxyimino-3-oxopentanoate (43.77 g).

Workup

  1. custom(40 minutes)
  2. stirringstirred for more 1.5 hours
  3. customquenched by aqueous sodium bicarbonate
  4. washThe organic phase was washed with brine
  5. dry with materialdried with magnesium sulfate
  6. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-7210aca65bd94136ac6f4bb13a613f1c
Source dataset
uspto-grants-1999_09
Patent number
US05958914

Reaction notes

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