Methyl acetoacetate → Methyl 3-(2,6-dichlorophenyl)-5-methylisoxazole-4-carboxylate

HRID 2047236Notes

Reaction equation

HRID 2047236 reaction equation
Cl[C:2](=[N:11][OH:12])[C:3]1[C:8]([Cl:9])=[CH:7][CH:6]=[CH:5][C:4]=1[Cl:10].C(N(C(C)C)CC)(C)C.O=[C:23]([CH3:29])[CH2:24][C:25]([O:27][CH3:28])=[O:26]>>[Cl:10][C:4]1[CH:5]=[CH:6][CH:7]=[C:8]([Cl:9])[C:3]=1[C:2]1[C:24]([C:25]([O:27][CH3:28])=[O:26])=[C:23]([CH3:29])[O:12][N:11]=1

Participants

4

Reactant 3

HCID 7757Methyl acetoacetateHCID 81531DiisopropylethylamineHCID 28001642,6-Dichlorobenzaldchloroxime

Product 1

HCID 619436Methyl 3-(2,6-dichlorophenyl)-5-methylisoxazole-4-carboxylateYield 87%

Procedure

To a solution of 0.1 g (0.4455 mmol) alpha-Chloro-2,6-dichlorobenzaldoxime in 5 mL methyl 3-oxobutanoate, 0.11 mL (1.5 eq) diisopropylethlamine were added. The mixture was stirred for 24 h then ethylacetate was removed in the vacuo. The residue was dried under high vacuo and the crude product was triturated in water until it became solid. The solid was filtered off and further purified by recrystallization from a water-methanol mixture. The crystals were filtered off, washed with water and dried under reduced pressure to afford 248 mg (87%) of methyl 3-(2,6-dichlorophenyl)-5-methylisoxazole-4-carboxylate. Result of LC/MS [M+H]+: 286.12; 1H NMR (DMSO-d6; CCl4): 2.77 (3H, s, CH3-isooxazole), 3.28 (3H, s, CH3-methoxy), 7.54-7.65 (3H, m, aromatic)

Workup

  1. customethylacetate was removed in the vacuo
  2. customThe residue was dried under high vacuo
  3. customthe crude product was triturated in water until it
  4. filtrationThe solid was filtered off
  5. customfurther purified by recrystallization from a water-methanol mixture
  6. filtrationThe crystals were filtered off
  7. washwashed with water
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-3dc7d3cf9a814951a1ba4c076764d903
Source dataset
uspto-grants-2013_11
Patent number
US08592456B2

Reaction notes

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