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

HRID 56533Notes

Reaction equation

HRID 56533 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

7

Reactant 4

HCID 10340Sodium CarbonateHCID 433294Lithium ChlorideHCID 2734357Furan-2-boronic acidHCID 86657503HCID 86657503, compound

Product 1

HCID 584320242-(3,5-Dimethoxy-4-methylphenyl)furanYield 77%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

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

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

Sources & evidence

ORD record
ord-c239cb1d86c04cea97b2f1f71abb3181
Source dataset
uspto-grants-2016_09
Patent number
US09434707B2

Reaction notes

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