反应详情

To a stirred suspension of trimethyl sulfoxonium chloride (3.78 g, 0.03 mole) in dry THF (60 ml) was added sodium hydride (1.16 g, 0.03 mole) and the whole warmed to reflux for 1 h. 2-Hydroxy-3-methyl-benzaldehyde (Lancaster) (4 g, 0.03 mole) was added in 30 ml THF via syringe and the resulting orange suspension stirred at reflux for 5 h. Water (50 ml) was added, and the organics were extracted with ether (3×50 ml). The combined organics were dried (MgSO4), filtered and evaporated in vacuo to an orange oil which was purified by column chromatography using 15-25% EtOAc in pentane to give the title product (2 g, 45%); 1HNMR (400 MHz, CDCl3) δ: 2.2 (s, 3H), 4.45 (m, 2H), 5.3 (m, 1H), 6.8 (t, 1H), 7.1 (d, 1H), 7.2 (d, 1H); LRMS: M+H, 151. (ES+).

1. temperaturethe whole warmed
2. temperatureto reflux for 1 h
3. temperatureat reflux for 5 h
4. extractionthe organics were extracted with ether (3×50 ml)
5. dry with materialThe combined organics were dried (MgSO4)
6. filtrationfiltered
7. customevaporated in vacuo to an orange oil which
8. customwas purified by column chromatography