Water → HCID 68815305, compound

Participants

Reaction Steps

To a stirring solution of (E)-1-(4-tert-butyldimethylsilyloxy-3-methoxyphenyl)-6,6-dimethylhept-1-ene-3,5-dione (700 mg, 1.79 mmol) in THF (15 ml) under N2 was added potassium tert-butoxide (442 mg, 3.94 mmol) and stirred for a further 45 min at room temperature. A solution of methyl iodide (0.235 ml, 3.76 mmol) in THF (2 ml) was added and the mixture heated at reflux for 5 h. Water (25 ml) was added to the cooled mixture followed by DCM (25 ml). The organic layer was separated, washed with water (25 ml), dried (MgSO4(anh)), filtered and concentrated. The residue was purified by column chromatography on silica using dichloromethane as eluent to give the monomethyl alkylated product, (E)-1-(4-tert-butyldimethylsilyloxy-3-methoxyphenyl)-4,6,6-trimethylhept-1-ene-3,5-dione (540 mg, 74%):

Provenance & Evidence