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

HRID 333363

Reaction equation

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

Participants

Conditions

Temperature: 50 °C

Procedure

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%.

Workup

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

Sources & evidence

ORD record: ord-7bf0b10118034bb1bb14191273d87519
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08877923B2

Linked notes

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