Hydrochloric Acid → 2-(3,5-Dimethylbiphenyl-4-yl)-4-[1-(tetrahydrofuran-3-yl)methylidene]-cyclopentane-1,3-dione
Reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:5]=[C:6]([CH3:23])[C:7]=1[C:8]1[C:9](=[O:22])[CH:10]([CH:15](O)[CH:16]2[CH2:20][CH2:19][O:18][CH2:17]2)[CH2:11][C:12]=1[O:13]C.Cl>CC(C)=O>[CH3:23][C:6]1[CH:5]=[C:4]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:3]=[C:2]([CH3:1])[C:7]=1[CH:8]1[C:9](=[O:22])[C:10](=[CH:15][CH:16]2[CH2:20][CH2:19][O:18][CH2:17]2)[CH2:11][C:12]1=[O:13]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 130 °C
Procedure
A mixture of 2-(3,5-Dimethylbiphenyl-4-yl)-5-[hydroxyl-(tetrahydrofuran-3-yl)-methyl]-3-methoxy-cyclopent-2-enone (1.1 g, 2.8 mmol), acetone (21 ml) and 2N hydrochloric acid (10 ml) is heated under microwave conditions at 130° C. for 40 minutes. The organic solvent is evaporated under vacuo, diluted with water (100 ml) and extracted with ethyl acetate (3×100 ml). The combined organic extracts are combined, washed with water and brine, dried over anhydrous sodium sulphate, filtered and the filtrate is concentrated in vacuo. The residue is purified by column chromatography on silica gel to give 2-(3,5-dimethylbiphenyl-4-yl)-4-[1-(tetrahydrofuran-3-yl)methylidene]-cyclopentane-1,3-dione (0.29 g).
Workup
- customThe organic solvent is evaporated under vacuo
- additiondiluted with water (100 ml)
- extractionextracted with ethyl acetate (3×100 ml)
- washwashed with water and brine
- dry with materialdried over anhydrous sodium sulphate
- filtrationfiltered
- concentrationthe filtrate is concentrated in vacuo
- customThe residue is purified by column chromatography on silica gel
Sources & evidence
- ORD record
- ord-83c6a5a6374942c6b5383562e3488258
- Source dataset
- uspto-grants-2015_08
- Patent number
- US09096560B2
Reaction notes
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