1-(4-Methoxyphenyl)butane-1,3-dione → 4-(4-Methoxybenzoyl)-5-methylisoxazole-3-carboxylic acid ethyl ester

HRID 887048

反応式

HRID 887048 の反応式
[O-]CC.[Na+].[CH3:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13](=[O:18])[CH2:14][C:15](=[O:17])[CH3:16])=[CH:9][CH:8]=1.Cl[C:20](=[N:26]O)[C:21]([O:23][CH2:24][CH3:25])=[O:22]>C(O)C>[CH2:24]([O:23][C:21]([C:20]1[C:14]([C:13](=[O:18])[C:10]2[CH:9]=[CH:8][C:7]([O:6][CH3:5])=[CH:12][CH:11]=2)=[C:15]([CH3:16])[O:17][N:26]=1)=[O:22])[CH3:25]

参加物

5

反応物 3

HCID 776401-(4-Methoxyphenyl)butane-1,3-dioneHCID 2723922Sodium ethoxideHCID 6816376Ethyl chloro(hydroximino)acetate

生成物 1

HCID 596520274-(4-Methoxybenzoyl)-5-methylisoxazole-3-carboxylic acid ethyl ester

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒4 回

実験手順

To 7.04 mL of 21% sodium ethoxide in ethanol (18.8 mmol) in 60 mL ethanol at 0° C. was added 4.70 g of 1-(4-methoxyphenyl)butane-1,3-dione (17.1 mmol) in 60 mL ethanol dropwise over 24 minutes. After 30 min a solution of 2.59 g of ethyl chloro-(hydroximino)acetate (17.1 mmol) in 30 mL ethanol was added dropwise over 6 minutes. The reaction was warmed to room temperature slowly. When TLC indicated the reaction was complete, the reaction was concentrated in vacuo. Water and saturated NaHCO3 was added and the product extracted with ethyl acetate. The ethyl acetate extracts were dried with Na2SO4, filtered, and concentrated in vacuo. The crude material was purified via silica gel chromatography eluting with 8:1 hexane:ethyl acetate to give 4-(4-methoxybenzoyl)-5-methylisoxazole-3-carboxylic acid ethyl ester which was dried overnight under high vacuum to give 3.74 g (71.8%).

後処理

  1. concentrationthe reaction was concentrated in vacuo
  2. additionWater and saturated NaHCO3 was added
  3. extractionthe product extracted with ethyl acetate
  4. dry with materialThe ethyl acetate extracts were dried with Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude material was purified via silica gel chromatography
  8. washeluting with 8:1 hexane

出典と根拠

ORDレコード
ord-8f43d294955747ae9d8d9980fb7b361b
出典データセット
uspto-grants-2012_08
特許番号
US08247414B2

関連ノート

読み込み中…