Sulfuric Acid → 1-(4-Methoxyphenyl)butane-1,3-dione

HRID 887047

反応式

HRID 887047 の反応式
[C:1](OCC)(=[O:3])[CH3:2].[H-].[Na+].[CH3:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([C:17](=[O:19])[CH3:18])=[CH:13][CH:12]=1.S(=O)(=O)(O)O>C1COCC1.C(O)C.C1OCCOCCOCCOCCOCCOC1>[CH3:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([C:17](=[O:19])[CH2:18][C:1](=[O:3])[CH3:2])=[CH:13][CH:12]=1

参加物

8

反応物 4

HCID 1118Sulfuric AcidHCID 74764'-MethoxyacetophenoneHCID 8857Ethyl AcetateHCID 24758Sodium hydride

生成物 1

HCID 776401-(4-Methoxyphenyl)butane-1,3-dione収率 60.5%

試薬・触媒・溶媒 3

HCID 702Ethanol触媒HCID 2855718-Crown-6触媒HCID 8028Tetrahydrofuran溶媒3 回

反応条件

温度
0 °C

実験手順

To 9.80 mL of ethyl acetate (100 mmol) in 40 mL dry THF at room temperature was added 2.0 g of 60% sodium hydride (49.9 mmol), 7.50 g of 4′-methoxyacetophenone (49.9 mmol), 100.0 mg of 18-crown-6 (0.40 mmol), and 2 drops of ethanol. After 30 minutes, the reaction was refluxed for 1 h, and then 100 mL of dry THF was added. After an additional 1 h, 30 mL THF was added. After 1 h the reaction was cooled to 0° C. and 25 mL of 10% aqueous sulfuric acid was added. The product was extracted with diethyl ether. The ether extracts were dried with Na2SO4, filtered, and concentrated in vacuo. The crude material was purified via silica gel chromatography eluting with 4:1 hexane:ethyl acetate to give 5.8 g of 1-(4-methoxyphenyl)butane-1,3-dione containing 30% starting material (via 1H NMR 42% yield).

後処理

  1. temperaturethe reaction was refluxed for 1 h
  2. waitAfter an additional 1 h
  3. extractionThe product was extracted with diethyl ether
  4. dry with materialThe ether extracts were dried with Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude material was purified via silica gel chromatography
  8. washeluting with 4:1 hexane

出典と根拠

ORDレコード
ord-daa254d9fbe14efb946f262df292762e
出典データセット
uspto-grants-2012_08
特許番号
US08247414B2

関連ノート

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