5-[Hydroxy-(tetrahydro-pyran-4-yl)-methyl]-3-methoxy-2-(2,4,6-trimethyl-phenyl)-cyclopent-2-enone → 4-[1-(Tetrahydro-pyran-4-yl)-meth-(e)-ylidene]-2-(2,4,6-trimethyl-phenyl)-cyclopentane-1,3-dione
Reaction equation
O[CH:2]([CH:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1)[CH:3]1[C:7](=[O:8])[C:6]([C:9]2[C:14]([CH3:15])=[CH:13][C:12]([CH3:16])=[CH:11][C:10]=2[CH3:17])=[C:5]([O:18]C)[CH2:4]1>CC(C)=O.Cl>[O:23]1[CH2:22][CH2:21][CH:20](/[CH:2]=[C:3]2/[C:7](=[O:8])[CH:6]([C:9]3[C:10]([CH3:17])=[CH:11][C:12]([CH3:16])=[CH:13][C:14]=3[CH3:15])[C:5](=[O:18])[CH2:4]/2)[CH2:25][CH2:24]1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 130 °C
Procedure
To a solution of 5-[hydroxy-(tetrahydro-pyran-4-yl)-methyl]-3-methoxy-2-(2,4,6-trimethyl-phenyl)-cyclopent-2-enone (408 mg, 1.18 mmol) in acetone (2 ml) is added a 2N solution of hydrochloric acid (2 ml) and the resulting solution is heated to 130° C. by microwave irradiation for 90 minutes. The reaction mixture was diluted with 2N hydrochloric acid (25 ml), and extracted with ethyl acetate (2×25 ml). The combined organics are washed with brine (25 ml), dried over magnesium sulphate, filtered and concentrated in vacuuo to give 4-[1-(tetrahydro-pyran-4-yl)-meth-(E)-ylidene]-2-(2,4,6-trimethyl-phenyl)-cyclopentane-1,3-dione (302 mg).
Workup
- extractionextracted with ethyl acetate (2×25 ml)
- washThe combined organics are washed with brine (25 ml)
- dry with materialdried over magnesium sulphate
- filtrationfiltered
- concentrationconcentrated in vacuuo
Sources & evidence
- ORD record
- ord-98fb14d74080475f9e20964a86cecfe6
- Source dataset
- uspto-grants-2015_08
- Patent number
- US09096560B2
Reaction notes
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