Ethyl Acetoacetate → Ethyl 3-(3-chlorophenyl)-5-methylisoxazole-4-carboxylate

HRID 332317Notes

Reaction equation

HRID 332317 reaction equation
[Na].[C:2]([O:8][CH2:9][CH3:10])(=[O:7])[CH2:3][C:4]([CH3:6])=[O:5].O/[N:12]=[C:13](\Cl)/[C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[CH:15]=1>CO>[CH2:9]([O:8][C:2]([C:3]1[C:13]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[CH:15]=2)=[N:12][O:5][C:4]=1[CH3:6])=[O:7])[CH3:10]

Participants

5

Reactant 3

HCID 8868Ethyl AcetoacetateHCID 5360545SodiumHCID 10943262alpha,3-Dichlorobenzaldoxime

Product 1

HCID 10901525Ethyl 3-(3-chlorophenyl)-5-methylisoxazole-4-carboxylateYield 40%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a suspension of sodium (2.67 g, 116 mmol) in methanol (100 mL) was added ethyl acetoacetate (12.8 g, 11.9 mL, 110 mmol) at room temperature over 15 minutes and then a a solution of (E)- and/or (Z)-N-hydroxy-3-chloro-benzenecarboximidoyl chloride (19.0 g, 100 mmol) in methanol (100 mL) was added over 20 minutes and the resulting mixture allowed to stir for 4 h at room temperature. The mixture was then poured onto water and cooled to 5° C., filtered and evaporated. Purification by recrystallisation from ethanol afforded the title compound (10.1 g, 40%) which was obtained as a white solid. Mp: 71-73° C.

Workup

  1. additionThe mixture was then poured onto water
  2. temperaturecooled to 5° C.
  3. filtrationfiltered
  4. customevaporated
  5. customPurification
  6. customby recrystallisation from ethanol

Sources & evidence

ORD record
ord-c7a9ba2bb72341fabfcdfcb1e509a309
Source dataset
uspto-grants-2014_11
Patent number
US08877783B2

Reaction notes

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