Acetonitrile → 3-Phenoxybenzyl 2-{4-(methoxycarbonylmethyloxy)phenyl}-2-methylpropyl ether

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Reaktionsgleichung

[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:26])([CH3:25])[CH2:9][O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH:13]=2)=[CH:4][CH:3]=1.[H-].[Na+].C(#N)C.Br[CH2:33][C:34]([O:36][CH3:37])=[O:35]>C(OCC)(=O)C>[CH3:37][O:36][C:34]([CH2:33][O:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([CH3:26])([CH3:25])[CH2:9][O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH:13]=2)=[CH:6][CH:7]=1)=[O:35]

Komponenten

Reaktionsbedingungen

Temperatur: 60 °C

Versuchsvorschrift

3-Phenoxybenzyl 2-(4-hydroxyphenyl)-2-methylpropyl ether (3.0 g), 0.36 g of sodium hydride and 20 ml of acetonitrile were heated under reflux for about 20 minutes, followed by the dropwise addition of 2 ml of methyl bromoacetate at room temperature. The resulting mixture was stirred at 60° C. for 20 minutes. After concentration of the reaction mixture, about 50 ml of ethyl acetate were added to the concentrate, followed by washing with water, drying and concentration. The resulting concentrate was fractionated and purified by chromatography on a silica gel column, whereby 3.0 g of 3-phenoxybenzyl 2-{4-(methoxycarbonylmethyloxy)phenyl}-2-methylpropyl ether were obtained.

Aufarbeitung

temperatureunder reflux for about 20 minutes
washby washing with water
customdrying
concentrationconcentration
concentrationThe resulting concentrate
custompurified by chromatography on a silica gel column

Quellen und Nachweise

ORD-Eintrag: ord-1b25b21ad460477f8a9e05a02affe9d9
Quelldatensatz: uspto-grants-1997_03
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05608104

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