反应详情

To a stirred suspension of 4-iodo-3-hydroxy-5,6,7,8-tetrahydro-2-naphthalenecarboxylic acid (23.43 g, 73.65 mmol) in dry acetone (450 mL) was added dimethyl sulfate (17.42 mL, 184.13 mmol) and K2CO3 (25.45 g, 184.13 mmol). The mixture was stirred at reflux overnight, cooled and triethylamine (40 mL) was added. After 0.5 h the mixture was filtered through a pad of diatomaceous earth and the filtrate concentrated in vacuo. The residue was dissolved in ethyl acetate (50 mL) and washed successively with 1N HCl (2×50 mL), sat. aqueous sodium bicarbonate (2×50 mL) and brine (50 mL ), dried (Na2SO4), filtered and concentrated in vacuo to afford a brown oil (22.52 g, 90%). 1H NMR (CDCl3) δ 7.56 (s, 1H), 3.92 (s, 3H), 3.85 (s, 3H), 2.69 (m, 4H), 1.79 (m, 4H). MS m/z 347 (M+H).

1. temperatureat reflux overnight
2. temperaturecooled
3. filtrationAfter 0.5 h the mixture was filtered through a pad of diatomaceous earth
4. concentrationthe filtrate concentrated in vacuo
5. dissolutionThe residue was dissolved in ethyl acetate (50 mL)
6. washwashed successively with 1N HCl (2×50 mL), sat. aqueous sodium bicarbonate (2×50 mL) and brine (50 mL )
7. dry with materialdried (Na2SO4)
8. filtrationfiltered
9. concentrationconcentrated in vacuo