1-Pentyl-1H-indole-2,3-dione → 3-(Benzo[d][1,3]dioxol-5-yl)-3-hydroxy-1-pentylindolin-2-one

HRID 1259562ノート

反応式

HRID 1259562 の反応式
[CH2:1]([N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8](=[O:15])[C:7]1=[O:16])[CH2:2][CH2:3][CH2:4][CH3:5].[CH2:17]1[O:25][C:24]2[C:19](=[CH:20][CH:21]=[C-:22][CH:23]=2)[O:18]1.[Mg+2].[Br-]>C1COCC1>[O:18]1[C:19]2[CH:20]=[CH:21][C:22]([C:8]3([OH:15])[C:9]4[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=4)[N:6]([CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])[C:7]3=[O:16])=[CH:23][C:24]=2[O:25][CH2:17]1

参加物

4

反応物 2

HCID 15810921-Pentyl-1H-indole-2,3-dioneHCID 44296443,4-(Methylenedioxy)phenylmagnesium bromide solution

生成物 1

HCID 120043373-(Benzo[d][1,3]dioxol-5-yl)-3-hydroxy-1-pentylindolin-2-one収率 71.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

To a solution of 1-pentyl-1H-indole-2,3-dione (2.80 g, 12.8 mmol) in THF (50.0 mL) was added 3,4-(methylenedioxy)phenylmagnesium bromide (14.0 mL, 1 M THF solution, 14.0 mmol) slowly at −78° C. The mixture was stirred at 0° C. for 1 h and quenched with ammonium chloride solution. The mixture was poured into water (150 mL) and extracted with ethyl acetate (200 mL). The organic layer was washed with water, dried over sodium sulfate and filtered. The filtrate was concentrated in vacuo to dryness. The residue was subjected to flash column chromatography to afford the title compound (3.10 g, 71%) as an orange oil: 1H NMR (300 MHz, CDCl3) δ 7.34-7.23 (m, 2H), 7.05 (t, 1H), 6.91-6.85 (m, 2H), 6.83-6.78 (m, 1H), 6.71 (d, 1H), 5.92-5.89 (m, 2H), 3.82-3.55 (m, 2H), 3.40 (br, 1H), 1.76-1.61 (m, 2H), 1.39-1.28 (m, 4H), 0.87 (t, 3H).

後処理

  1. customquenched with ammonium chloride solution
  2. additionThe mixture was poured into water (150 mL)
  3. extractionextracted with ethyl acetate (200 mL)
  4. washThe organic layer was washed with water
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated in vacuo to dryness

出典と根拠

ORDレコード
ord-206e4510b65049f7b5c4f5ca25caac23
出典データセット
uspto-grants-2013_06
特許番号
US08466188B2

反応ノート

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