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

HRID 1259562노트

반응식

HRID 1259562 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-206e4510b65049f7b5c4f5ca25caac23
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08466188B2

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