Tetrahydrofuran → 4-(2,6-Diethyl-4-methylphenyl)-5-hydroxy-2,6-dimethyl-3(2H)-pyridazinone

HRID 508586

反応式

HRID 508586 の反応式
O1CCCC1.CC(C)([O-])C.[K+].[CH2:12]([C:14]1[CH:19]=[C:18]([CH3:20])[CH:17]=[C:16]([CH2:21][CH3:22])[C:15]=1[CH2:23][C:24]([N:26]([CH3:35])[N:27]=[C:28]([CH3:34])[C:29]([O:31]CC)=O)=[O:25])[CH3:13].C(OCC)(=O)C>C1(C)C=CC=CC=1.CCCCCC>[CH2:21]([C:16]1[CH:17]=[C:18]([CH3:20])[CH:19]=[C:14]([CH2:12][CH3:13])[C:15]=1[C:23]1[C:24](=[O:25])[N:26]([CH3:35])[N:27]=[C:28]([CH3:34])[C:29]=1[OH:31])[CH3:22]

参加物

7

反応物 4

HCID 8028TetrahydrofuranHCID 8857Ethyl AcetateHCID 23665647Potassium tert-butoxideHCID 76550641Ethyl 2-[2-(2,6-diethyl-4-methylphenylacetyl)-2-methylhydrazono]propanoate

生成物 1

HCID 546837784-(2,6-Diethyl-4-methylphenyl)-5-hydroxy-2,6-dimethyl-3(2H)-pyridazinone収率 46.4%

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 8058Hexane溶媒

実験手順

Under a nitrogen atmosphere, 13 mL of a tetrahydrofuran solution of potassium tert-butoxide (1 mol/L) was stirred at room temperature, to which a solution of 1.9 g of ethyl 2-[2-(2,6-diethyl-4-methylphenylacetyl)-2-methylhydrazono]propanoate (Compound VI-2) in 55 mL of toluene was added dropwise over about 1 hour. The mixture was further stirred at room temperature for 30 minutes. Then, the reaction mixture was concentrated under reduced pressure. To the residue obtained was added 30 mL of ice-water, which was extracted with tert-butyl methyl ether (20 mL×2). To the aqueous layer was then added 1.6 g of 35% hydrochloric acid, which was extracted with ethyl acetate (20 mL×3). The ethyl acetate extracts were combined, washed with saturated sodium chloride aqueous solution (20 mL×2), dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue obtained was subjected to a silica gel column chromatography (ethyl acetate:hexane=1:3 as eluent) to yield 0.76 g of a solid. The solid was washed with cold hexane and air-dried to yield 0.59 g of the title compound as white powder.

後処理

  1. additionwas added dropwise over about 1 hour
  2. concentrationThen, the reaction mixture was concentrated under reduced pressure
  3. customTo the residue obtained
  4. extractionwas extracted with tert-butyl methyl ether (20 mL×2)
  5. additionTo the aqueous layer was then added 1.6 g of 35% hydrochloric acid, which
  6. extractionwas extracted with ethyl acetate (20 mL×3)
  7. washwashed with saturated sodium chloride aqueous solution (20 mL×2)
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customThe residue obtained

出典と根拠

ORDレコード
ord-d94c6c10b9ef456cb610d74df78cab10
出典データセット
uspto-grants-2015_08
特許番号
US09096533B2

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