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

HRID 1805265노트

반응식

HRID 1805265 반응식
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

참가 물질

4

반응물 3

HCID 7757Methyl acetoacetateHCID 81531DiisopropylethylamineHCID 28001642,6-Dichlorobenzaldchloroxime

생성물 1

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

실험 절차

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)

후처리

  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

출처 및 근거

ORD 기록
ord-f8a28c3e898c4ffd88a5bd5a2a6ff565
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08354436B2

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