Water → HCID 68817206, compound

Participants

Reaction Steps

To a stirring solution of (E)-1-(4-tert-butyldimethylsilyloxy-3-methoxyphenyl)-4,6,6-trimethylhept-1-ene-3,5-dione (540 mg, 1.33 mmol) in THF (10 ml) under N2 was added sodium hydride (64 mg (of 60%), 1.60 mmol) and stirred for a further 45 min at room temperature. A solution of methyl iodide (0.1 ml, 1.60 mmol) in THF (1 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 (E)-1-(4-tert-butyldimethylsilyloxy-3-methoxyphenyl)-4,4,6,6-tetramethylhept-1-ene-3,5-dione (266 mg, 48%) as a yellow oil: 1H NMR (400 MHz, CDCl3) δ 0.17 (6H, s, Si(CH3)2), 0.99 (9H, s, SiC(CH3)3), 1.18 (9H, s, C(CH3)3), 1.41 (6H, s, 2×C(CH3)), 3.83 (3H, s, OCH3), 6.54 (1H, d, J=15.6 Hz, vinyl CH), 6.84 (1H, d, J=8.0 Hz, ArH), 6.98 (1H, d, J=2.0 Hz, ArH), 7.06 (1H, dd, J=8.0, 2.0 Hz, ArH), 7.66 (1H, d, J=15.6 Hz, vinyl CH) ppm.

Provenance & Evidence