1,2-Dimethoxyethane → 5-(4-Hydroxyphenyl)-2-methylfuran-3-carbaldehyde

HRID 1877192Notes

Reaction equation

HRID 1877192 reaction equation
Br[C:2]1[O:6][C:5]([CH3:7])=[C:4]([CH:8]=[O:9])[CH:3]=1.[OH:10][C:11]1[CH:16]=[CH:15][C:14](B(O)O)=[CH:13][CH:12]=1.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.O>[OH:10][C:11]1[CH:16]=[CH:15][C:14]([C:2]2[O:6][C:5]([CH3:7])=[C:4]([CH:8]=[O:9])[CH:3]=2)=[CH:13][CH:12]=1

Participants

7

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 27343604-Hydroxyphenylboronic acidHCID 469416735-Bromo-2-methylfuran-3-carbaldehyde

Product 1

HCID 866463915-(4-Hydroxyphenyl)-2-methylfuran-3-carbaldehydeYield 78.7%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Procedure

A mixture of 5-bromo-2-methylfuran-3-carbaldehyde (1.9 g), 4-hydroxyphenylboronic acid (1.7 g), tetrakis(triphenylphosphine)palladium(0) (0.6 g), 2N aqueous sodium carbonate solution (12 mL) and 1,2-dimethoxyethane (50 mL) was stirred overnight with refluxing under an argon atmosphere. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (0% ethyl acetate/hexane to 35% ethyl acetate/hexane) to give the title compound (1.6 g, 35%) as a yellow crystal.

Workup

  1. temperaturewith refluxing under an argon atmosphere
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel chromatography (0% ethyl acetate/hexane to 35% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-8fdb9b878c9f457c865e56238ad55314
Source dataset
uspto-grants-2012_11
Patent number
US08309580B2

Reaction notes

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