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Ethyl Acetate → 3-bromo-2-(ethoxycarbonyl)-1-isobutyl-1H-indole-5-carboxylic acid

HRID 2249694
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인쇄 미리보기

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HRID 2249694 반응식
[Br:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([CH:11]=[O:12])[CH:9]=2)[N:4]([CH2:13][CH:14]([CH3:16])[CH3:15])[C:3]=1[C:17]([O:19][CH2:20][CH3:21])=[O:18].O.O.P([O-])(O)(O)=[O:25].[Na+].Cl([O-])=O.[Na+].C(OCC)(=O)C>C(#N)C.O.OO>[Br:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]([OH:25])=[O:12])[CH:9]=2)[N:4]([CH2:13][CH:14]([CH3:15])[CH3:16])[C:3]=1[C:17]([O:19][CH2:20][CH3:21])=[O:18]
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참가 물질

8

반응물 4

HCID 8857Ethyl AcetateHCID 17816525ethyl 3-bromo-5-formyl-1-isobutyl-1H-indole-2-carboxylateHCID 23668197Sodium ChloriteHCID 23673460Sodium Phosphate, Monobasic, Dihydrate

생성물 1

HCID 178165173-bromo-2-(ethoxycarbonyl)-1-isobutyl-1H-indole-5-carboxylic acid수율 54.4%

시약·촉매·용매 3

HCID 784
Hydrogen Peroxide
용매
HCID 962Water용매3회
HCID 6342Acetonitrile용매

반응 조건

온도
60 °C

실험 절차

In 7 ml of acetonitrile is dissolved 0.65 g of ethyl 3-bromo-5-formyl-1-isobutyl-1H-indole-2-carboxylate. To the solution are successively added at ambient temperature 1.56 g of sodium dihydrogen-phosphate dihydrate dissolved in 22 ml of water and 0.64 ml of 30% aqueous hydrogen peroxide. Then, 0.68 g of sodium chlorite dissolved in 20 ml of water is dropwise added thereto at 5-10° C. The mixture thus obtained is stirred at 60° C. for one hour. Ethyl acetate and water are added to the reaction mixture, 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 then the solvent is distilled off under reduced pressure. Thus, 0.37 g of 3-bromo-2-(ethoxycarbonyl)-1-isobutyl-1H-indole-5-carboxylic acid is obtained as a yellow solid product.

후처리

  1. additionis dropwise added
  2. customat 5-10° C
  3. customThe mixture thus obtained
  4. customthe organic layer is separated
  5. customThe organic layer thus obtained
  6. washis washed with water and saturated aqueous solution of sodium chloride successively
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationthe solvent is distilled off under reduced pressure

출처 및 근거

ORD 기록
ord-335ce303a31d4215a8775af4f11aeec7
출처 데이터셋
uspto-grants-2008_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07314888B1

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