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

HRID 225952

反応式

HRID 225952 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 8471Triethylamine触媒HCID 6344Dichloromethane溶媒2 回

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-427150645de04ad59bb5ae8c4cc2ae4b
出典データセット
uspto-grants-2009_07
特許番号
US07557133B2

関連ノート

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