Hydrochloric Acid → 3-[4-(5-Methoxy-2-methyl-phenoxy)-2-methyl-phenyl]-acrylic acid ethyl ester

HRID 1822342

Reaktionsgleichung

[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH3:10])=[C:7]([OH:9])[CH:8]=1.[CH2:11]([O:13][C:14](=[O:25])[CH:15]=[CH:16][C:17]1[CH:22]=[CH:21][C:20](F)=[CH:19][C:18]=1[CH3:24])[CH3:12].C(=O)([O-])[O-].[K+].[K+].Cl>CS(C)=O>[CH2:11]([O:13][C:14](=[O:25])[CH:15]=[CH:16][C:17]1[CH:22]=[CH:21][C:20]([O:9][C:7]2[CH:8]=[C:3]([O:2][CH3:1])[CH:4]=[CH:5][C:6]=2[CH3:10])=[CH:19][C:18]=1[CH3:24])[CH3:12]

Komponenten

Reaktionsbedingungen

Temperatur: 140 °C

Versuchsvorschrift

The compounds of 5-methoxy-2-methyl-phenol (1.46 g, 9.60 mmol), 3-(4-fluoro-2-methyl-phenyl)-acrylic acid ethyl ester (1.00 g, 4.80 mmol), potassium carbonate (1.33 g, 9.60 mmol) are dissolved in dimethylsulfoxide (12 mL) under nitrogen, and the mixture is stirred overnight at 140° C. HCl 10% is added, and the mixture is extracted with diethyl ether. The organic layer is washed with water, dried (Na2SO4) and filtered, and then the solvent is evaporated in vacuo. Purification by flash chromatography by eluting with hexane:ethyl acetate 10:1 to afford the title compound (0.74 g, 47%). Rf=0.44 (hexane:ethyl acetate 5:1). 1H NMR (300 MHz, CDCl3): δ1.34 (t, 3H, J=7.3 Hz), 2.13 (s, 3H), 2.40 (s, 3H), 3.74 (s, 3H), 4.26 (q, 2H, J=7.1 Hz), 6.28 (d, 1H, J=15.9 Hz), 6.53 (d, 1H, J=2.4 Hz), 6.66-6.73 (m, 3H), 7.15 (d, 1H, J=8.3 Hz), 7.51 (d, 1H, J=8.3 Hz), 7.93 (d, 1H, J=16.0 Hz).

Aufarbeitung

extractionthe mixture is extracted with diethyl ether
washThe organic layer is washed with water
dry with materialdried (Na2SO4)
filtrationfiltered
customthe solvent is evaporated in vacuo
customPurification by flash chromatography
washby eluting with hexane:ethyl acetate 10:1

Quellen und Nachweise

ORD-Eintrag: ord-026c8309746a46508710020b08ba8d96
Quelldatensatz: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07608639B2

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