Water → Ethyl 3-(1,3-dimethyl-1H-indol-2-yl)-5-ethyl-4,5-dihydro-5-isoxazole-carboxylate

HRID 225952

반응식

HRID 225952 반응식
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH3:11])=[C:3]1[CH:12]=[N:13][OH:14].[CH2:15]([C:17](=[CH2:23])[C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH3:16].Cl[O-].[Na+].O>ClCCl.C(N(CC)CC)C>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH3:11])=[C:3]1[C:12]1[CH2:23][C:17]([CH2:15][CH3:16])([C:18]([O:20][CH2:21][CH3:22])=[O:19])[O:14][N:13]=1

참가 물질

7

반응물 4

HCID 962WaterHCID 291416Ethyl 2-methylidenebutanoateHCID 23665760Sodium HypochloriteHCID 852718921,3-Dimethyl-1H-indol-2-aldehyde oxime

생성물 1

HCID 68835063Ethyl 3-(1,3-dimethyl-1H-indol-2-yl)-5-ethyl-4,5-dihydro-5-isoxazole-carboxylate수율 35.3%

시약·촉매·용매 2

HCID 8471Triethylamine촉매HCID 6344Dichloromethane용매2회

실험 절차

1,3-Dimethyl-1H-indol-2-aldehyde oxime derivative (356 mg, 2.07 mmol) was dissolved in dichloromethane (20 ml), and the mixture was kept at 0□. Ethyl 2-ethylacrylate (345 mg, 1.3 Eq) and triethylamine (6 drops) were dissolved in dichloromethane (5 ml), thus obtained solution was slowly added to the above, and sodium hypochlorite solution (5.5 ml) was further added. The reaction solution was warmed to room temperature and stirred for 4 hours. Water (20 ml) was added, and the mixture was extracted with dichloromethane (40 ml×2), washed with aqueous sodium chloride solution (20 ml), dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography (15% ethyl acetate-hexane) to give the title compound (230 mg, Yield 35%).

후처리

  1. additionwas further added
  2. extractionthe mixture was extracted with dichloromethane (40 ml×2)
  3. washwashed with aqueous sodium chloride solution (20 ml)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography (15% ethyl acetate-hexane)

출처 및 근거

ORD 기록
ord-427150645de04ad59bb5ae8c4cc2ae4b
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07557133B2

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