Hexen-2-al → Diethyl 4-n-propylpyridine-2,3-dicarboxylate

HRID 1936695

反応式

HRID 1936695 の反応式
Cl[CH:2]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[C:3](=O)[C:4]([O:6][CH2:7][CH3:8])=[O:5].[CH3:15][C:16](=O)[CH:17]=[CH:18][CH2:19][CH3:20].S(=O)(=O)([O-])[NH2:23].[NH4+]>C(O)C>[CH2:17]([C:18]1[CH:19]=[CH:20][N:23]=[C:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])[C:2]=1[C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH2:16][CH3:15]

参加物

5

反応物 3

HCID 12990Hexen-2-alHCID 24482Ammonium sulfamateHCID 10998635Diethyl 2-chloro-3-oxobutanedioate

生成物 1

HCID 22462372Diethyl 4-n-propylpyridine-2,3-dicarboxylate収率 21%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A solution of diethyl 3-chloro-2-oxosuccinate (137.4 g, 0.69 mol), hexen-2-al (72.5 g, 0.74 mol) and ammonium sulphamate (190.2 g, 1.66 mol) in ethanol (450 ml) was stirred under reflux for 36 hours and then filtered. The filtrate was evaporated under vacuum, the resulting residue dissolved in water (500 ml) and this solution extracted with ethyl acetate (6×500 ml). The combined organic extracts were dried (MgSO4) and evaporated under vacuum, then the resulting residue was chromatographed on silica gel (50 g), using an ethyl acetate in hexane elution gradient (0-20% ethyl acetate), to give the title compound as an orange oil (34.1 g, 21%). Rf 0.20 (ethyl acetate:hexane, 20:80).

後処理

  1. temperatureunder reflux for 36 hours
  2. filtrationfiltered
  3. customThe filtrate was evaporated under vacuum
  4. dissolutionthe resulting residue dissolved in water (500 ml)
  5. extractionthis solution extracted with ethyl acetate (6×500 ml)
  6. dry with materialThe combined organic extracts were dried (MgSO4)
  7. customevaporated under vacuum
  8. customthe resulting residue was chromatographed on silica gel (50 g)
  9. washan ethyl acetate in hexane elution gradient (0-20% ethyl acetate)

出典と根拠

ORDレコード
ord-cc0872dd258b48ea86be6a68f141cca7
出典データセット
uspto-grants-2002_05
特許番号
US06391885B1

関連ノート

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