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

HRID 2047236ノート

反応式

HRID 2047236 の反応式
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

参加物

4

反応物 3

HCID 7757Methyl acetoacetateHCID 81531DiisopropylethylamineHCID 28001642,6-Dichlorobenzaldchloroxime

生成物 1

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

実験手順

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)

後処理

  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

出典と根拠

ORDレコード
ord-3dc7d3cf9a814951a1ba4c076764d903
出典データセット
uspto-grants-2013_11
特許番号
US08592456B2

反応ノート

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