Ethyl isobutyrylacetate → HCID 178472908, compound

HRID 253333Notes

Reaction equation

HRID 253333 reaction equation
[CH3:1][CH:2]([CH3:11])[C:3](=[O:10])[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].[N:12]([O-])=[O:13].[Na+]>C(O)(=O)C.O>[OH:13][N:12]=[C:4]([C:3](=[O:10])[CH:2]([CH3:1])[CH3:11])[C:5]([O:7][CH2:8][CH3:9])=[O:6]

Participants

5

Reactant 2

HCID 81583Ethyl isobutyrylacetateHCID 23668193Sodium Nitrite

Product 1

HCID 178472908HCID 178472908, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×

Procedure

42.4 g of ethyl 4-methyl-3-oxopentanoate are dissolved in 100 ml of glacial acetic acid, and 21 g of sodium nitrite, dissolved in 100 ml of water, are added at 5° C. Over a period of one hour, the mixture is allowed to warm to room temperature, 100 ml of water are added and the mixture is stirred at room temperature for another hour. The mixture is extracted three times with in each case 150 ml of methyl tert-butyl ether, 200 ml of water are added to the combined organic phases and the mixture is neutralized by addition of solid NaHCO3. The organic phase is removed, washed with saturated NaCl solution and dried over MgSO4, and the solvent is removed under reduced pressure. This gives 46 g of ethyl 2-hydroxyimino-4-methyl-3-oxopentanoate as an oil. C8H13NO4 (187.20), MS (ESI)=188 (M+H+).

Workup

  1. additionare added at 5° C
  2. extractionThe mixture is extracted three times with in each case 150 ml of methyl tert-butyl ether, 200 ml of water
  3. additionare added to the combined organic phases
  4. additionthe mixture is neutralized by addition of solid NaHCO3
  5. customThe organic phase is removed
  6. washwashed with saturated NaCl solution
  7. dry with materialdried over MgSO4
  8. customthe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-883b8fb85d984780b01898ea739fd812
Source dataset
uspto-grants-2011_01
Patent number
US07872034B2

Reaction notes

Loading…