Water → Ethyl 3-butyl-1-methyl-1H-indole-5-carboxylate

HRID 14212

반응식

HRID 14212 반응식
[CH2:1]([C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:12]=2)[NH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4].[CH3:19]C(C)([O-])C.[K+].IC.O>CS(C)=O>[CH2:1]([C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:12]=2)[N:7]([CH3:19])[CH:6]=1)[CH2:2][CH2:3][CH3:4]

참가 물질

6

반응물 4

HCID 962WaterHCID 6328Methyl iodideHCID 21086100ethyl 3-butyl-1H-indole-5-carboxylateHCID 23665647Potassium tert-butoxide

생성물 1

HCID 21086101Ethyl 3-butyl-1-methyl-1H-indole-5-carboxylate수율 46.3%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

반응 조건

온도
50 °C

실험 절차

To a mixture of ethyl 3-butyl-1H-indole-5-carboxylate (0.6 g) in methylsulfoxide (10 mL) was added potassium t-butoxide (0.29 g) and iodomethane (2.0 mL). The mixture was stirred at 50° C. for 18 H, at which time the mixture was pored into water (50 mL). The solution was extracted with ethyl acetate and the organic extracts washed three times with brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. Column chromatography on silica gel (100 mL) using 5% ethyl acetate in hexanes as eluent to give 0.294 g of the title compound: 1H NMR (CDCl3) δ 0.953, 1.44, 1.69, 2.77, 3.76, 4.40, 6.87, 7.26, 7.91, 8.35.

후처리

  1. extractionThe solution was extracted with ethyl acetate
  2. washthe organic extracts washed three times with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-114c48f6863b4162903239d87df55f74
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07727997B2

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