Water → 1,7-Diacetyl-4-methoxyindoline

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Reaktionsgleichung

[C:1]([N:4]1[C:12]2[C:7](=[C:8]([O:13][CH3:14])[CH:9]=[CH:10][CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[C:15](Cl)(=[O:17])[CH3:16].[Al+3].[Cl-].[Cl-].[Cl-].O>ClCCCl.CCOCC.CCOC(C)=O>[C:1]([N:4]1[C:12]2[C:7](=[C:8]([O:13][CH3:14])[CH:9]=[CH:10][C:11]=2[C:15](=[O:17])[CH3:16])[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Komponenten

Reaktionsbedingungen

Temperatur: 50 °C

Versuchsvorschrift

To a solution of 1-acetyl-4-methoxyindoline (4.02 g, 21 mmol) in dry 1,2-dichloroethane (30 ml) cooled in ice was added acetyl chloride (2.1 ml, 30 mmol). Powdered anhydrous AlCl3 (8.4 g, 63 mmol) was added portionwise with stirring. The mixture was stirred at rt overnight, then warmed to 50° C. for 2 h. The red/brown slurry was poured into acidified cold water (200 ml) and extracted with CH2Cl2. The combined organic phases were washed with 0.5 M aq. NaOH and brine, dried and evaporated to give a brown oil. Flash chromatography (EtOAc) followed by trituration with Et2O afforded 22 as pale yellow needles (2.22 g, 54%), mp 88-89° C., (Found: C, 66.89; H, 6.50; N, 5.95. C13H15NO3 requires C, 66.94; H, 6.48; N, 6.00%); δH (90 MHz) 7.33 (1 H, d, J 8.3, H-5), 6.61 (1 H, d, H-6), 4.17 (2 H, t, J 8.1, H-2), 3.85 (3 H, s, OMe), 3.05 (2 H, t, 3-H), 2.44 (3 H, s, 7-Ac) and 2.21 (3 H, s, N-Ac).

Aufarbeitung

stirringThe mixture was stirred at rt overnight
additionThe red/brown slurry was poured
extractionextracted with CH2Cl2
washThe combined organic phases were washed with 0.5 M aq. NaOH and brine
customdried
customevaporated
customto give a brown oil

Quellen und Nachweise

ORD-Eintrag: ord-15423bcfc264408f91a5252ab45575f7
Quelldatensatz: uspto-grants-2004_07
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06765014B1

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