Toluene → 5-(3,4,5-Trimethoxyphenyl)thiophene-2-carboaldehyde

HRID 993035Notes

Reaction equation

HRID 993035 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5](B(O)O)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].Cl[C:17]1[S:21][C:20]([CH:22]=[O:23])=[CH:19][CH:18]=1.C1(C)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>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.C(OCC)(=O)C.C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:17]2[S:21][C:20]([CH:22]=[O:23])=[CH:19][CH:18]=2)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10]

Participants

8

Reactant 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 817002-Thiophenecarboxaldehyde, 5-chloro-HCID 27343903,4,5-Trimethoxybenzeneboronic acid

Product 1

HCID 184084975-(3,4,5-Trimethoxyphenyl)thiophene-2-carboaldehyde

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

3,4,5-Trimethoxyphenylboronic acid (848 mg) and 5-chlorothiophene-2-carboaldehyde (764 mg) were suspended in a mixed solvent of toluene (20 mL) and THF (15 mL), and to the suspension 2 M sodium carbonate (8 mL) was added. Tetrakis(triphenylphosphine)palladium(0) (231 mg) was added to the mixture under an argon atmosphere, and the mixture was stirred at 90° C. for 5 hours as it is. After allowing the reaction mixture to cool, ethyl acetate was added to the reaction mixture to separate an organic layer. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=5:1) to obtain the title compound.

Workup

  1. temperatureto cool
  2. customto separate an organic layer
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-e47029a5d45a4a10aba5c3005b8b31f4
Source dataset
uspto-grants-2002_10
Patent number
US06472386B1

Reaction notes

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