Potassium Carbonate → 7-Methylbenzofuran-5-ol

HRID 920123Notes

Reaction equation

HRID 920123 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([CH3:12])[C:6]2[O:10][CH:9]=[CH:8][C:7]=2[CH:11]=1.C([O-])([O-])=O.[K+].[K+].[Si](I)(C)(C)C>C(#N)C.CCOC(C)=O>[CH3:12][C:5]1[C:6]2[O:10][CH:9]=[CH:8][C:7]=2[CH:11]=[C:3]([OH:2])[CH:4]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 85247Trimethylsilyl iodideHCID 680164105-Methoxy-7-methylbenzofuran

Product 1

HCID 846492027-Methylbenzofuran-5-olYield 26%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of the product from Step D (850 mg, 5.2 mmol) and K2CO3 in acetonitrile (10 mL) was added TMSI (1.1 mL). The mixture was refluxed for 2 hrs. The reaction was cooled to room temperature. The mixture was diluted with EtOAc (100 mL) and washed with brine (30 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluted with PE:EtOAc=5:1) to afford the title compound (200 mg, 25%) as an oil.

Workup

  1. temperatureThe mixture was refluxed for 2 hrs
  2. washwashed with brine (30 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluted with PE:EtOAc=5:1)

Sources & evidence

ORD record
ord-ece00ddd972745a3a3baf62717440247
Source dataset
uspto-grants-2016_03
Patent number
US09273046B2

Reaction notes

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