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

Participants

Reaction Conditions

Reaction Steps

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).

Provenance & Evidence