Sodium Carbonate → 2-(3,5-Dimethoxy-4-methylphenyl)furan

HRID 512632Notes

Reaction equation

FC(F)(F)S(O[C:7]1[CH:12]=[C:11]([O:13][CH3:14])[C:10]([CH3:15])=[C:9]([O:16][CH3:17])[CH:8]=1)(=O)=O.[O:20]1[CH:24]=[CH:23][CH:22]=[C:21]1B(O)O.[Li+].[Cl-].C([O-])([O-])=O.[Na+].[Na+]>COCCOC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:17][O:16][C:9]1[CH:8]=[C:7]([C:21]2[O:20][CH:24]=[CH:23][CH:22]=2)[CH:12]=[C:11]([O:13][CH3:14])[C:10]=1[CH3:15]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 3,5-dimethoxy-4-methylphenyl trifluoromethanesulfonate (0.50 g, 1.67 mmol) in DME (15 mL) was added 2-furylboronic acid (0.245 g, 2.2 mmol), LiCl (0.149 g, 3.5 mmol), 2 M aqueous Na2CO3 (1.8 mL, 3.6 mmol) and tetrakis(triphenylphosphine)palladium (0.098 g, 0.085 mmol) and the mixture was degassed as described previously. The reaction was heated at 80° C. under argon for 22 hrs. After cooling to room temperature, the reaction was diluted with H2O and extracted with EtOAc. The combined organics were washed with H2O, saturated aqueous NH4Cl, H2O and brine, dried over Na2SO4 and concentrated in vacuo. Purification by chromatography (0-25% Et2O-hexanes) gave 2-(3,5-dimethoxy-4-methylphenyl)furan as a white solid (0.28 g, 77% yield).

Workup

customthe mixture was degassed
temperatureAfter cooling to room temperature
additionthe reaction was diluted with H2O
extractionextracted with EtOAc
washThe combined organics were washed with H2O, saturated aqueous NH4Cl, H2O and brine
dry with materialdried over Na2SO4
concentrationconcentrated in vacuo
customPurification by chromatography (0-25% Et2O-hexanes)

Sources & evidence

ORD record: ord-9533601fae1e44fdb8c62acc23e623b6
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09102643B2

Reaction notes

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