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Dicyclohexylcarbodiimide → Ethyl 4-[(5,5-dimethyl-8-(carbethoxymethyl)-5,6-dihydronaphthalen-2-yl)azo]benzoate

HRID 963886
ノート
印刷プレビュー

反応式

HRID 963886 の反応式
[CH3:1][C:2]1([CH3:32])[CH2:11][CH2:10][C:9](O)([CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:8]2[CH:7]=[C:6]([N:19]=[N:20][C:21]3[CH:31]=[CH:30][C:24]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:23][CH:22]=3)[CH:5]=[CH:4][C:3]1=2.C1CCC(N=C=NC2CCCCC2)CC1>C1C=CC=CC=1.Cl[Cu]>[CH3:32][C:2]1([CH3:1])[CH2:11][CH:10]=[C:9]([CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:8]2[CH:7]=[C:6]([N:19]=[N:20][C:21]3[CH:22]=[CH:23][C:24]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:30][CH:31]=3)[CH:5]=[CH:4][C:3]1=2
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 10868DicyclohexylcarbodiimideHCID 22571557(+/-) Ethyl 4-[(5,5-dimethyl-8-hydroxy-8-carbethoxymethy5,6,7,8-tetrahydronaphth-2-yl)azo]benzoate2 回

生成物 1

HCID 22571504Ethyl 4-[(5,5-dimethyl-8-(carbethoxymethyl)-5,6-dihydronaphthalen-2-yl)azo]benzoate

試薬・触媒・溶媒 2

HCID 62652Cuprous chloride触媒HCID 241Benzene
溶媒

実験手順

A solution of (+/-) ethyl 4-[(5,5-dimethyl-8-hydroxy-8-carbethoxymethyl-5,6,7,8-tetrahydronaphth-2-yl)azo]benzoate (Compound D1, 108 mg, 0.25 mmol), DCC (55.9 mg, 0.271 mmol) and CuCl (36.6 mg, 0.37 mmol) in 8 ml of dry benzene was heated under reflux for 7 days. After cooling to room temperature, the solids were filtered out and the solution was extracted with ethyl acetate. The combined organic layer was washed with brine and dried over Na2 SO4. The solvent was removed under reduced pressure, the crude material was purified by flash chromatography (silicagel, 10% ethyl acetate in hexane) to afford the pure title compounds as red oils.

後処理

  1. temperatureunder reflux for 7 days
  2. filtrationthe solids were filtered out
  3. extractionthe solution was extracted with ethyl acetate
  4. washThe combined organic layer was washed with brine
  5. customdried over Na2 SO4
  6. customThe solvent was removed under reduced pressure
  7. customthe crude material was purified by flash chromatography (silicagel, 10% ethyl acetate in hexane)

出典と根拠

ORDレコード
ord-b7b32bd7eb894933a26b44f46fcb114e
出典データセット
uspto-grants-1998_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05763635

反応ノート

読み込み中…

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