(2,4-Dimethyl-1,3-thiazol-5-yl)methanol

Synthesis

General procedure for the synthesis of (2,4-dimethyl-1,3-thiazol-5-yl)methanol from ethyl 2,4-dimethylthiazole-5-carboxylate: ethyl 2,4-dimethylthiazole-5-carboxylate (500 mg, 2.70 mmol) was dissolved in anhydrous tetrahydrofuran (10 mL), and lithium aluminium hydroxide (205 mg, 5.40 mmol) was slowly added at 0 °C. After the reaction lasted for 1 h, the reaction was quenched by careful addition of water (10 mL). Subsequently, the reaction mixture was extracted with ethyl acetate (15 mL x 3), the organic phases were combined and dried over anhydrous sodium sulfate. After concentration under reduced pressure, the reaction was purified by preparative thin layer chromatography (TLC) plates (unfolding reagent ratio 1:1 petroleum ether/ethyl acetate, Rf = 0.4) to afford the target product (2,4-dimethyl-1,3-thiazol-5-yl)methanol (300 mg, yellow solid) in 77% yield.1H NMR (400 MHz, methanol-d4) δ: 4.68 (s, 2H) 2.64 (s, 3H), 2.33 (s, 3H).

References

[1] Patent: EP3299371, 2018, A1. Location in patent: Paragraph 0252; 0253; 0254
[2] Journal of Medicinal Chemistry, 1973, vol. 16, p. 978 - 984
[3] Patent: EP1186604, 2002, A1. Location in patent: Page 131-132