Water → Ethyl 3-(benzothiophen-2-yl)-5-ethyl-4,5-dihydro-5-isoxazolecarboxylate

HRID 225951

反応式

HRID 225951 の反応式
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[CH:10]=[N:11][OH:12].[CH2:13]([C:15](=[CH2:21])[C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH3:14].Cl[O-].[Na+].O>C1COCC1.C(N(CC)CC)C>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[C:10]1[CH2:21][C:15]([CH2:13][CH3:14])([C:16]([O:18][CH2:19][CH3:20])=[O:17])[O:12][N:11]=1

参加物

7

反応物 4

HCID 962WaterHCID 291416Ethyl 2-methylidenebutanoateHCID 23665760Sodium HypochloriteHCID 85255485Benzothiophen-2-aldehyde oxime

生成物 1

HCID 68829660Ethyl 3-(benzothiophen-2-yl)-5-ethyl-4,5-dihydro-5-isoxazolecarboxylate収率 18%

試薬・触媒・溶媒 2

HCID 8471Triethylamine触媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

Benzothiophen-2-aldehyde oxime derivative (400 mg, 2.26 mmol) prepared according to the same procedure as Preparation 1 was dissolved in THF (25 ml), and the mixture was kept at 0□. Ethyl 2-ethylacrylate (434 mg, 1.5 Eq) and triethylamine (7 drops) were dissolved in THF (5 ml), thus obtained solution was slowly added to the above, and sodium hypochlorite solution (6.0 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 ethyl acetate (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 (20% ethyl acetate-hexane) to give the title compound (121 mg, Yield 18%).

後処理

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

出典と根拠

ORDレコード
ord-e2fa1e311a79428eb715b292d4618aea
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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