Ethylene Glycol → Diethyl 2-acetamido-2-{2-[4-(1,1-ethylenedioxy-5-phenylpentyl)phenyl]ethyl}malonate

HRID 1795708ノート

反応式

HRID 1795708 の反応式
[CH2:1]([O:3][C:4](=[O:35])[C:5]([NH:31][C:32](=[O:34])[CH3:33])([CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([C:19](=[O:30])[CH2:20][CH2:21][CH2:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH:15][CH:14]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH3:2].[CH2:36](O)[CH2:37][OH:38].C1(C)C=CC(S(O)(=O)=O)=CC=1.C(N(CC)CC)C>C1C=CC=CC=1.C(OCC)(=O)C>[C:32]([NH:31][C:5]([CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2([O:38][CH2:37][CH2:36][O:30]2)[CH2:20][CH2:21][CH2:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH:15][CH:14]=1)([C:6]([O:8][CH2:9][CH3:10])=[O:7])[C:4]([O:3][CH2:1][CH3:2])=[O:35])(=[O:34])[CH3:33]

参加物

7

反応物 4

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 8471TriethylamineHCID 22178485Diethyl 2-acetamido-2-{2-[4-(1-oxo-5-phenylpentyl)phenyl]ethyl}malonate

生成物 1

HCID 21026720Diethyl 2-acetamido-2-{2-[4-(1,1-ethylenedioxy-5-phenylpentyl)phenyl]ethyl}malonate

試薬・触媒・溶媒 2

HCID 241Benzene溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A solution of diethyl-2-acetamido-2-{2-[4-(1-oxo-5-phenylpentyl)phenyl]ethyl}malonate (13.5 g), ethylene glycol (3.1 ml) and p-toluenesulfonic acid (0.53 g) in benzene (135 ml) was refluxed under heating for 20 hours, while dehydrating with Dean-Stark trap. The reaction mixture was treated with triethylamine (2.4 ml) and ethyl acetate (200 ml) was added thereto. The mixture was washed with water and saturated brine, dried over anhydrous sodium sulfate and the solvent was distilled away under reduced pressure to give a pale yellow oily substance (15.9 g). The obtained pale yellow oily substance was purified by silica gel column chromatography (eluent; hexane:ethyl acetate=1:1) to give diethyl 2acetamido-2-{2-[4-(1,1-ethylenedioxy-5-phenylpentyl)phenyl]ethyl}malonate (14.1 g) as a colorless transparent oily substance.

後処理

  1. temperatureunder heating for 20 hours
  2. additionwas added
  3. washThe mixture was washed with water and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationthe solvent was distilled away under reduced pressure
  6. customto give a pale yellow oily substance (15.9 g)
  7. customThe obtained pale yellow oily substance was purified by silica gel column chromatography (eluent; hexane:ethyl acetate=1:1)

出典と根拠

ORDレコード
ord-95ff72409f764794a1e7dc705fd1f1f8
出典データセット
uspto-grants-2006_04
特許番号
USRE039072E1

反応ノート

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