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

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Reaktionsgleichung

[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

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

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).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag: ord-faa675765cf543528e03f60cfd27fce6
Quelldatensatz: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07700641B2

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