反应详情

温度

0 °C

To a suspension of lithium aluminum hydride (52 mg, 1.25 mmol) in diethyl ether (2 mL) under argon was added 2-(2-thienyl)thiazole-5-carboxylic acid ethyl ester (lit: Robba, M., LeGuen, Y., Bull. Soc. Chim. Fr., 1969(5)1762; 0.3 g, 1.25 mmol) at 0° C. The reaction mixture was allowed to equilibrate to room temperature and was stirred for 24 h. The reaction was re-cooled to 0° C. and was quenched by the careful addition of saturated aqueous ammonium chloride solution dropwise until no further reaction was apparent. The resulting solids were recovered by filtration, washed with diethyl ether and retained for further processing (vide infra). The filtrate was washed with brine, dried (MgSO4), filtered and concentrated under reduced pressure. The solids that were recovered from the ammonium chloride quench were then slurried in ethyl acetate, filtered and washed with ethyl acetate. The resulting filtrate was washed with brine, dried (MgSO4), filtered and evaporated reduced pressure. The solid residues obtained from the work up of both the diethyl ether filtrate and the ethyl acetate filtrate were combined to yield 179 mg (72% yield) of 2-(2-thienyl)thiazole-5-methanol as a yellow solid.

1. customto equilibrate to room temperature
2. customwas quenched by the careful addition of saturated aqueous ammonium chloride solution dropwise until no further reaction
3. filtrationThe resulting solids were recovered by filtration
4. washwashed with diethyl ether
5. washThe filtrate was washed with brine
6. dry with materialdried (MgSO4)
7. filtrationfiltered
8. concentrationconcentrated under reduced pressure
9. customThe solids that were recovered from the ammonium chloride
10. customquench
11. filtrationfiltered
12. washwashed with ethyl acetate
13. washThe resulting filtrate was washed with brine
14. dry with materialdried (MgSO4)
15. filtrationfiltered
16. customevaporated reduced pressure
17. customThe solid residues obtained from the work up of both the diethyl ether filtrate