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

HRID 965505

反応式

HRID 965505 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

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-89059a86f56045c59e305364c57bb848
出典データセット
uspto-grants-1998_06
特許番号
US05773594

関連ノート

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