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Oxalyl chloride → ethyl 5-(2,4-diisobutoxybenzoyl)-1-isobutyl-1H-indole-2-carboxylate

HRID 2249651
ノート
印刷プレビュー

反応式

HRID 2249651 の反応式
[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH2:18][CH:19]([CH3:21])[CH3:20])[C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([C:15]([OH:17])=O)=[CH:10][CH:9]=2)=[O:5])[CH3:2].C(Cl)(=O)C(Cl)=O.[Cl-].[Al+3].[Cl-].[Cl-].[CH2:32]([O:36][C:37]1[CH:42]=[CH:41][CH:40]=[C:39]([O:43][CH2:44][CH:45]([CH3:47])[CH3:46])[CH:38]=1)[CH:33]([CH3:35])[CH3:34]>C(Cl)Cl.C(Cl)(Cl)Cl.CN(C)C=O>[CH2:44]([O:43][C:39]1[CH:38]=[C:37]([O:36][CH2:32][CH:33]([CH3:35])[CH3:34])[CH:42]=[CH:41][C:40]=1[C:15]([C:11]1[CH:12]=[C:13]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:18][CH:19]([CH3:21])[CH3:20])[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])=[CH:14]2)=[O:17])[CH:45]([CH3:47])[CH3:46]
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 65578Oxalyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 130875651,3-DiisobutoxybenzeneHCID 178165142-(ethoxycarbonyl)-1-isobutyl-1H-indole-5-carboxylic acid

生成物 1

HCID 17816510ethyl 5-(2,4-diisobutoxybenzoyl)-1-isobutyl-1H-indole-2-carboxylate収率 87.9%

試薬・触媒・溶媒 3

HCID 6212
Chloroform
溶媒
HCID 6228Dimethylformamide溶媒
HCID 6344Dichloromethane溶媒

実験手順

In 3 ml of methylene chloride is dissolved 0.12 g of 2-(ethoxycarbonyl)-1-isobutyl-1H-indole-5-carboxylic acid, to which are successively added 50 μl of oxalyl chloride and 20 μl of N,N-dimethylformamide at ambient temperature. The mixture is stirred at ambient temperature for one hour. Then, at 5-10° C., 0.12 g of aluminum chloride and 0.13 g of 1,3-diisobutoxybenzene are successively added and stirred at the same temperature as above for 30 minutes. The reaction mixture is added to a mixture of chloroform and ice water, and the organic layer is separated. The organic layer thus obtained is washed with water and saturated aqueous solution of sodium chloride successively and dried over anhydrous magnesium sulfate, and the solvent is distilled off under reduced pressure. The residue thus obtained is purified by silica gel column chromatography (eluent; hexane:ethyl acetate=1:1) to obtain 0.18 g of ethyl 5-(2,4-diisobutoxybenzoyl)-1-isobutyl-1H-indole-2-carboxylate as a colorless oily product.

後処理

  1. customat ambient temperature
  2. stirringstirred at the same temperature as above for 30 minutes
  3. customthe organic layer is separated
  4. customThe organic layer thus obtained
  5. washis washed with water and saturated aqueous solution of sodium chloride successively
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationthe solvent is distilled off under reduced pressure
  8. customThe residue thus obtained
  9. customis purified by silica gel column chromatography (eluent; hexane:ethyl acetate=1:1)

出典と根拠

ORDレコード
ord-85f7b9ce6568471d80f43608732b69fe
出典データセット
uspto-grants-2008_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07314888B1

反応ノート

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