Methyl iodide → 7-Methoxy-1,1-dimethyl-3,4-dihydronaphthalen-2(1H)-one

Participants

Reaction Conditions

Reaction Steps

To a solution of 7-methoxy-1-methyl-3,4-dihydro-1H-naphthalen-2-one (1.95 g, 10.3 mmol) in THF (30 ml) was added NHMDS (11.3 mmol, 11.3 ml, 1M in THF) at 0° C. under nitrogen. The resulted solution was stirred at 0° C. for 1 hr. Iodomethane (7.29 g, 3.19 ml, 51.3 mmol) was added and stirred for an additional 3 hrs. 10% KHSO4 aqueous solution was added to acidify the reaction mixture, diluted with brine, extracted with ethylacetate, washed with brine, dried over MgSO4, filtered. The filtrate was evaporated under vacuo. The residue was purified by chromatography using ethylacetate:hexane (0.9:9.5) as eluant to give the desired product as white solid. (1.77 g, 85%). 1H NMR (CDCl3) δ: 7.08(d, 1H, J=8.3 Hz), 6.88(d, 1H, J=2.7 Hz), 6.74(dd, 1H, J=2.7 and 8.3 Hz), 3.80(s, 3H), 3.03(t, 2H, J=6.6 Hz), 2.65(t, 2H, J=6.6 Hz), 1.42(s, 6H). 13C NMR (CDCl3) δ: 213.7, 157.8, 143.9, 128.1, 126.5, 111.3, 110.4, 54.4, 46.9, 36.5, 26.8, 25.8.

Provenance & Evidence