Ethyl 3-oxovalerate → HCID 178472905, compound

HRID 1274967Notes

Reaction equation

HRID 1274967 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-0a6d82296fc448e0bb667b8590001fad
Source dataset
uspto-grants-2000_12
Patent number
US06159961

Reaction notes

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