Acetone → 5-(4-Bromo-2,6-dimethylphenyl)-4-hydroxycyclopent-2-enone
Reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([C:9]2[CH:13]=[CH:12][O:11][C:10]=2[CH2:14]O)=[C:4]([CH3:16])[CH:3]=1.CC(C)=[O:19]>O>[Br:1][C:2]1[CH:3]=[C:4]([CH3:16])[C:5]([CH:9]2[C:10](=[O:11])[CH:14]=[CH:12][CH:13]2[OH:19])=[C:6]([CH3:8])[CH:7]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 55 °C
Procedure
Polyphosphoric acid (500 mg) is added to a warm (55° C.) solution of ([4-bromo-2,6-dimethylphenyl]furan-2-yl)methanol (843 mg, 3 mmol) in acetone (8 ml) and water (2 ml) and the mixture is heated at 55° C. for 24 hours. The mixture is cooled to room temperature and the acetone is removed under reduced pressure. The remaining mixture is partitioned between diethyl ether (20 ml) and water (20 ml). The aqueous phase is extracted with ether (2×50 ml), and then the organic phases are combined, washed with saturated aqueous sodium bicarbonate solution (20 ml), and brine (20 ml), dried over anhydrous magnesium sulfate, filtered and the filtrate is evaporated under reduced pressure. The residue is purified by column chromatography on silica gel to give 5-(4-bromo-2,6-dimethylphenyl)-4-hydroxycyclopent-2-enone (596 mg).
Workup
- temperatureThe mixture is cooled to room temperature
- customthe acetone is removed under reduced pressure
- customThe remaining mixture is partitioned between diethyl ether (20 ml) and water (20 ml)
- extractionThe aqueous phase is extracted with ether (2×50 ml)
- washwashed with saturated aqueous sodium bicarbonate solution (20 ml), and brine (20 ml)
- dry with materialdried over anhydrous magnesium sulfate
- filtrationfiltered
- customthe filtrate is evaporated under reduced pressure
- customThe residue is purified by column chromatography on silica gel
Sources & evidence
- ORD record
- ord-8abbc7d961744bd688b50bda39744e23
- Source dataset
- uspto-grants-2014_03
- Patent number
- US08680339B2
Reaction notes
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