Sesamol → 7-bromo-3-hydroxy-3-(6-hydroxy-1,3-benzodioxol-5-yl)-1,3-dihydro-2H-indol-2-one

HRID 1965297ノート

反応式

HRID 1965297 の反応式
[CH2:1]1[O:5][C:4]2[CH:6]=[C:7]([OH:10])[CH:8]=[CH:9][C:3]=2[O:2]1.C([Mg]Cl)(C)C.[Br:16][C:17]1[CH:18]=[CH:19][CH:20]=[C:21]2[C:25]=1[NH:24][C:23](=[O:26])[C:22]2=[O:27]>O1CCCC1.[Cl-].[NH4+].C(OCC)(=O)C>[Br:16][C:17]1[CH:18]=[CH:19][CH:20]=[C:21]2[C:25]=1[NH:24][C:23](=[O:26])[C:22]2([OH:27])[C:8]1[C:7]([OH:10])=[CH:6][C:4]2[O:5][CH2:1][O:2][C:3]=2[CH:9]=1

参加物

7

反応物 3

HCID 68289SesamolHCID 23023537-BromoisatinHCID 178418918HCID 178418918、化合物

生成物 1

HCID 673574857-bromo-3-hydroxy-3-(6-hydroxy-1,3-benzodioxol-5-yl)-1,3-dihydro-2H-indol-2-one収率 77%

試薬・触媒・溶媒 3

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒HCID 25517Ammonium Chloride溶媒

反応条件

温度
0 °C

実験手順

To a solution of sesamol (7.32 g, 53.1 mmol) in anhydrous tetrahydrofuran (150 mL) were added a solution of isopropylmagnesium chloride (2.0 M in tetrahydrofuran, 30.1 mL, 60.2 mmol) at 0° C. under nitrogen. The reaction mixture was stirred at 0° C. for 30 min, followed by the addition of 7-bromo isatin (8.0 g, 35.4 mmol). The suspended mixture was stirred at ambient temperature for 16 h. The reaction mixture was diluted with a saturated aqueous solution of ammonium chloride (300 mL) and ethyl acetate (250 mL), and the phases were separated. The aqueous phase was extracted with ethyl acetate (200 mL), and the combined organic solution was washed with brine (100 mL), dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The crude solid was triturated with diethyl ether, filtered and dried under the reduced pressure to afford 7-bromo-3-hydroxy-3-(6-hydroxy-1,3-benzodioxol-5-yl)-1,3-dihydro-2H-indol-2-one (9.8 g, 77%) as a light yellow solid: 1H NMR (300 MHz, DMSO-d6) δ10.64 (s, 1H), 9.18 (s, 1H), 7.33 (dd, J=7.8, 1.4 Hz, 1H), 7.21 (s, 1H), 6.84-6.75 (m, 2H), 6.54 (s, 1H), 6.21 (s, 1H), 5.92 (dd, J=6.1, 0.8 Hz, 2H); MS (ES+) m/z 363.8 (M+1), 365.8 (M+1).

後処理

  1. stirringThe suspended mixture was stirred at ambient temperature for 16 h
  2. customthe phases were separated
  3. extractionThe aqueous phase was extracted with ethyl acetate (200 mL)
  4. washthe combined organic solution was washed with brine (100 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude solid was triturated with diethyl ether
  9. filtrationfiltered
  10. customdried under the reduced pressure

出典と根拠

ORDレコード
ord-22a9f8934b814587881a4d1907e6e143
出典データセット
uspto-grants-2013_04
特許番号
US08415370B2

反応ノート

読み込み中…