Ethyl Acetate → (Dimethyl-1,3-thiazol-5-yl)methanol

Temperature

0 °C

To a suspension of lithium aluminum hydride (563 mg, 14.8 mmol) in diethyl ether (25 mL) at 0° C. was added ethyl-2,4-dimethylthiazole-5-carboxylate (2.5 g, 13.5 mmol) in three portions. The reaction mixture was allowed to stir at 0° C. for 10 min, then at room temperature for 24 h. Ethyl acetate (65 mL) was added very slowly dropwise at 0° C. The reaction mixture was then added slowly to an aqueous solution of potassium sodium tartrate (30% w/v; 20 mL) and stirred for 2 h. The layers were separated and the aqueous layer was re-extracted with ethyl acetate (1×30 mL). The combined organic layers were dried (MgSO4), filtered, evaporated under reduced pressure. The resulting colorless solid was dried under high vacuum to give 2,4-dimethylthiazole-5-methanol (1.7 g, 91% yield). This material was used in a subsequent step without further purification.

1. waitat room temperature for 24 h
2. stirringstirred for 2 h
3. customThe layers were separated
4. extractionthe aqueous layer was re-extracted with ethyl acetate (1×30 mL)
5. dry with materialThe combined organic layers were dried (MgSO4)
6. filtrationfiltered
7. customevaporated under reduced pressure
8. customThe resulting colorless solid was dried under high vacuum

ORD record

ord-d85fac8774ac422582c6725eb42a1bd3

Source dataset

uspto-grants-2003_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06515124B2