反应详情

温度

80 °C

A mixture of Intermediate 103 (6.6 g, 40.9 mmol) and chloroacetone (FLUKA, 3.27 mL, 40.9 mmol) in DMF (50 mL) was stirred at 80° C. for 5 h. Reaction mixture was cooled to room temperature, treated with NaHCO3 (150 mL) and extracted with ethyl ether (2×200 mL). Organic layer was washed with brine, dried over Na2SO4 and evaporated to give title compound (7.57 g, 38.0 mmol, 93% yield) as yellow oil. 1H NMR (300 MHz, DMSO-d6) δ ppm: 7.19 (s, 1H), 4.23-4.06 (m, 3H), 2.31 (s, 3H), 1.48 (d, 3H), 1.16 (t, 3H). [ES+MS] m/z 200 (MH+). It was subsequently observed that this compound undergoes autooxidation at the stereogenic centre to form ethyl 2-hydroxy-2-(4-methyl-1,3-thiazol-2-yl)propanoate. Once the presence of this compound had been observed, the compound was actively synthesised, hereinbelow described as Intermediate 106.

1. customReaction mixture
2. temperaturewas cooled to room temperature
3. extractionextracted with ethyl ether (2×200 mL)
4. washOrganic layer was washed with brine
5. dry with materialdried over Na2SO4
6. customevaporated