Potassium Carbonate → 7-Methylbenzofuran-5-ol
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]=1Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
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
- temperatureThe mixture was refluxed for 2 hrs
- washwashed with brine (30 mL)
- dry with materialdried over anhydrous sodium sulfate
- concentrationconcentrated under reduced pressure
- 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
Loading…