Cesium carbonate → tert-butyl 2-(1-benzyl-2-ethyl-1H-indol-4-yloxy)acetate

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Reaktionsgleichung

[CH2:1]([C:3]1[N:4]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:5]2[C:10]([CH:11]=1)=[C:9]([OH:12])[CH:8]=[CH:7][CH:6]=2)[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29]>CN(C=O)C.O>[C:31]([O:30][C:28](=[O:29])[CH2:27][O:12][C:9]1[CH:8]=[CH:7][CH:6]=[C:5]2[C:10]=1[CH:11]=[C:3]([CH2:1][CH3:2])[N:4]2[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([CH3:34])([CH3:33])[CH3:32]

Komponenten

Reaktionsbedingungen

Temperatur: 35 °C

Versuchsvorschrift

2-Ethyl-4-hydroxy-1-(phenylmethyl)-1H-indole (5.82 g, 20 mmol) was added to 7.82 g (24 mmol) cesium carbonate in 25 mL DMF and the mixture stirred at 35° C. for 30 minutes. After cooling to 20° C., a solution of tert-butyl bromoacetate (4.65 g, 23.8 mmol) in 5 mL DMF was added and stirring maintained until the reaction was judged complete by TLC analysis (several hours). The mixture was diluted with water and extracted with ethyl acetate. The ethyl acetate solution was washed with brine, dried (MgSO4) and concentrated at reduced pressure to give 6.8 g of solid. Mass spectrum: 365

Aufarbeitung

temperatureAfter cooling to 20° C.
stirringstirring
temperaturemaintained until the reaction
customwas judged complete by TLC analysis (several hours)
extractionextracted with ethyl acetate
washThe ethyl acetate solution was washed with brine
dry with materialdried (MgSO4)
concentrationconcentrated at reduced pressure

Quellen und Nachweise

ORD-Eintrag: ord-bd2d314d894b4cb18901d38a0e32777e
Quelldatensatz: uspto-grants-2002_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06451839B1

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