(4-Methoxyphenyl)boronic acid → 4-(4-methoxyphenyl)-5,5-dimethylfuran-2(5H)-one

HRID 383483

Reaktionsgleichung

FC(F)(F)S(O[C:7]1[C:8]([CH3:14])([CH3:13])[O:9][C:10](=[O:12])[CH:11]=1)(=O)=O.[CH3:17][O:18][C:19]1[CH:24]=[CH:23][C:22](B(O)O)=[CH:21][CH:20]=1.[F-].[K+]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1(C)C=CC=CC=1.O>[CH3:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([C:7]2[C:8]([CH3:14])([CH3:13])[O:9][C:10](=[O:12])[CH:11]=2)=[CH:21][CH:20]=1

Komponenten

Reaktionsbedingungen

Temperatur: 50 °C

Versuchsvorschrift

To a 1:1 mixture of toluene/water (20 mL), were added 2,2-dimethyl-5-oxo-2,5-dihydrofuran-3-yl trifluoromethanesulfonate (100 mg, 0.38 mmol), 4-methoxyphenylboronic acid (87 mg, 0.57 mmol), PdCl2(PPh3)2 (27 mg, 0.038 mmol), 2M KF aqueous solution (0.95 mL, 1.9 mmol), benzyltriethylammonium chloride (8.7 mg, 0.038 mmol). The mixture was heated at 50° C. under N2 for 30 minutes, cooled to room temperature and extracted with EtOAc (2×50 mL). The organic layers were combined, washed with saturated NaHCO3 (50 mL) and brine (50 mL), dried over Na2SO4. Purification through silica gel column with 10-30% EtOAc/hexanes led to the product as yellow solid. Yield: 33 mg, 40%.

Aufarbeitung

temperaturecooled to room temperature
extractionextracted with EtOAc (2×50 mL)
washwashed with saturated NaHCO3 (50 mL) and brine (50 mL)
dry with materialdried over Na2SO4
customPurification through silica gel column with 10-30% EtOAc/hexanes

Quellen und Nachweise

ORD-Eintrag: ord-e2663724bba84f1bb0566abf2e0d5651
Quelldatensatz: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08367664B2

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