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

HRID 221849

반응식

HRID 221849 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매4회

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-61dc1495a4384999961add7a19d8179b
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08207168B2

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