Ethyl Acetoacetate → HCID 15682534, compound

HRID 1590005Notes

Reaction equation

HRID 1590005 reaction equation
[C:1]([O:7][CH2:8][CH3:9])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].[H-].[Na+].[CH3:12][O:13][C:14](=[O:19])[C:15](Cl)=[N:16]O>C1(C)C=CC=CC=1>[CH2:8]([O:7][C:1]([C:2]1[C:15]([C:14]([O:13][CH3:12])=[O:19])=[N:16][O:4][C:3]=1[CH3:5])=[O:6])[CH3:9]

Participants

5

Reactant 3

HCID 8868Ethyl AcetoacetateHCID 24758Sodium hydrideHCID 85058881HCID 85058881, compound

Product 1

HCID 15682534HCID 15682534, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

At room temperature, 39.0 g (0.3 mol) of ethyl acetoacetate in 100 ml of toluene was dripped into 9.9 g (0.33 mol) of NaH (80% strength suspension in white oil), and the mixture was stirred for 3 hours. Subsequently, 41.3 g (0.3 mol) of methyl-α-chloro-α-oximinoacetate in 100 ml of toluene was added and the mixture was stirred for 12 hours at room temperature. The reaction mixture was then transferred to a Soxhlet apparatus (extraction tube filled with 4 Å molecular sieve), 1 g of methanesulfonic acid was added and the mixture was refluxed for 1.5 hours. After the mixture had cooled, the organic phase was washed once with 200 ml of disodium bicarbonate solution and once with 200 ml of saturated sodium chloride solution and dried over magnesium sulfate, and the solvent was stripped off under reduced pressure.

Workup

  1. customAt room temperature
  2. stirringthe mixture was stirred for 12 hours at room temperature
  3. extractionThe reaction mixture was then transferred to a Soxhlet apparatus (extraction tube filled with 4 Å molecular sieve), 1 g of methanesulfonic acid
  4. additionwas added
  5. temperaturethe mixture was refluxed for 1.5 hours
  6. temperatureAfter the mixture had cooled
  7. washthe organic phase was washed once with 200 ml of disodium bicarbonate solution and once with 200 ml of saturated sodium chloride solution
  8. dry with materialdried over magnesium sulfate

Sources & evidence

ORD record
ord-ff1a4006ea9242b3854561230a650cfb
Source dataset
uspto-grants-1993_04
Patent number
US05201932

Reaction notes

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