Methyl iodide → 4-Methoxy-1-(2-methoxyethyl)-2-nitrobenzene

HRID 1914692

Reaktionsgleichung

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][OH:11])=[C:5]([N+:12]([O-:14])=[O:13])[CH:4]=1.[H-].[Na+].I[CH3:18]>C1COCC1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][O:11][CH3:18])=[C:5]([N+:12]([O-:14])=[O:13])[CH:4]=1

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

To a solution of 2-(4-methoxy-2-nitrophenyl)ethanol (1 g; 5.07 mmol; 1 eq) in THF (50 mL) is added sodium hydride (406 mg; 10.14 mmol; 2 eq) at 0° C. and the reaction mixture is stirred at 0° C. for 10 min before adding iodomethane (0.63 mL; 10.14 mmol; 2 eq). The reaction mixture is stirred overnight. It is quenched by addition of water. The product is extracted with EtOAc and the organic phase is dried over MgSO4. The solvent is evaporated under reduced pressure and the residue is purified by flash chromatography using a mixture of petrol ether and EtOAc (70/30) as eluent. The solvents are evaporated to afford 680 mg (63%) of the title compound as a yellow solid. 1H NMR (DMSO-d6) δ 7.35 (d, J=3.0 Hz, 1H), 7.21 (d, J=9.0 Hz, 1H), 6.98 (dd, J=9.0, 3.0 Hz, 1H), 3.76 (s, 3H), 3.54 (t, J=9.0 Hz, 2H), 3.24 (s, 314), 3.01 (t, J=9.0 Hz, 2H), HPLC (max plot) 94%; Rt 4.18 min.

Aufarbeitung

stirringThe reaction mixture is stirred overnight
customIt is quenched by addition of water
extractionThe product is extracted with EtOAc
dry with materialthe organic phase is dried over MgSO4
customThe solvent is evaporated under reduced pressure
customthe residue is purified by flash chromatography
additiona mixture of petrol ether and EtOAc (70/30) as eluent
customThe solvents are evaporated

Quellen und Nachweise

ORD-Eintrag: ord-a9506a830cbe4985be59d28e7bf0d98c
Quelldatensatz: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08614215B2

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