Triethylamine → 1-(4-Methoxycarbonylphenyl)-4-(4-n-pentyloxyphenyl)butane-1,4-dione

HRID 351539

反応式

HRID 351539 の反応式
[CH2:1]([O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]([CH:15]=[CH2:16])=[O:14])=[CH:9][CH:8]=1)[CH2:2][CH2:3][CH2:4][CH3:5].[CH:17]([C:19]1[CH:28]=[CH:27][C:22]([C:23]([O:25][CH3:26])=[O:24])=[CH:21][CH:20]=1)=[O:18].C(N(CC)CC)C>[Cl-].C([N+]1C(C)=C(CCO)SC=1)C1C=CC=CC=1.C(O)C>[CH3:26][O:25][C:23]([C:22]1[CH:27]=[CH:28][C:19]([C:17](=[O:18])[CH2:16][CH2:15][C:13]([C:10]2[CH:9]=[CH:8][C:7]([O:6][CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])=[CH:12][CH:11]=2)=[O:14])=[CH:20][CH:21]=1)=[O:24]

参加物

6

反応物 3

HCID 8471TriethylamineHCID 15294Methyl 4-FormylbenzoateHCID 227132221-(4-n-Pentyloxyphenyl)acrolein

生成物 1

HCID 227132231-(4-Methoxycarbonylphenyl)-4-(4-n-pentyloxyphenyl)butane-1,4-dione収率 81.8%

試薬・触媒・溶媒 2

HCID 28333523-Benzyl-5-(2-hydroxyethyl)-4-methylthiazolium chloride触媒HCID 702Ethanol溶媒

実験手順

A suspension of 1-(4-n-pentyloxyphenyl)acrolein (2.38 g), methyl 4-formylbenzoate (1.97 g), 3-benzyl-5-(2-hydroxyethyl)-4-methylthiazolium chloride and triethylamine (0.91 ml) in ethanol (10 ml) was refluxed for 18 hours. After cooling, the solvents were removed under reduced pressure. The solids were taken up in 1N HCl and extracted with dichloromethane. The organic layer was washed successively with water and brine, dried over magnesium sulfate and evaporated under reduced pressure. The residue was triturated with diisopropyl ether, collected by filtration and dried under reduced pressure to give 1-(4-methoxycarbonylphenyl)-4-(4-n-pentyloxyphenyl)butane-1,4-dione (3.41 g).

後処理

  1. temperaturewas refluxed for 18 hours
  2. temperatureAfter cooling
  3. customthe solvents were removed under reduced pressure
  4. extractionextracted with dichloromethane
  5. washThe organic layer was washed successively with water and brine
  6. dry with materialdried over magnesium sulfate
  7. customevaporated under reduced pressure
  8. customThe residue was triturated with diisopropyl ether
  9. filtrationcollected by filtration
  10. customdried under reduced pressure

出典と根拠

ORDレコード
ord-1dfc266d3ef0430ca5d5774187bb1e33
出典データセット
uspto-grants-2004_06
特許番号
US06743776B2

関連ノート

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