Diethyl Ether → 8-Methoxymethoxy-2,2,4-trimethyl-1,2-dihydro-6-oxa-1-azachrysen-5-one

HRID 1043673Notizen

Reaktionsgleichung

[OH:1][C:2]1[CH:3]=[C:4]2[C:17](=[CH:18][CH:19]=1)[C:16]1[C:7](=[C:8]3[C:13](=[CH:14][CH:15]=1)[NH:12][C:11]([CH3:21])([CH3:20])[CH:10]=[C:9]3[CH3:22])[C:6](=[O:23])[O:5]2.C(=O)([O-])[O-].[K+].[K+].[C:30]([O:33][CH2:34]C)(=O)C.C(OCC)C>CN(C)C=O>[CH3:30][O:33][CH2:34][O:1][C:2]1[CH:3]=[C:4]2[C:17](=[CH:18][CH:19]=1)[C:16]1[C:7](=[C:8]3[C:13](=[CH:14][CH:15]=1)[NH:12][C:11]([CH3:20])([CH3:21])[CH:10]=[C:9]3[CH3:22])[C:6](=[O:23])[O:5]2

Komponenten

Reaktionsbedingungen

Temperatur: 50 °C

Versuchsvorschrift

A mixture of 8-hydroxy-2,2,4-trimethyl-1,2-dihydro-6-oxa-1-azachrysen-5-one (Reference Compound No. 1-(4), 1.00 g, 3.25 mmol), chlorodimethylether (420 μL, 5.53 mmol) and potassium carbonate (1.35 g, 9.77 mmol) was suspended in anhydrous N,N-dimethylformamide (15 mL) and the suspension was stirred at 50° C. overnight. After cooling down, ethyl acetate (100 mL) and diethylether (100 mL) were added thereto. The whole was washed with water (150 mL, 100 mL) and saturated brine (100 mL) successively, dried over anhydrous magnesium sulfate, and then the solvent was removed under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate) to give the titled reference compound (747 mg) as a yellow solid. (Yield 66%)

Aufarbeitung

temperatureAfter cooling down
washThe whole was washed with water (150 mL, 100 mL) and saturated brine (100 mL) successively
dry with materialdried over anhydrous magnesium sulfate
customthe solvent was removed under reduced pressure
customThe obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Quellen und Nachweise

ORD-Eintrag: ord-f4c9a8ecc7c944298409d2cfe1f2abf0
Quelldatensatz: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08563551B2

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