反应详情

温度

-78 °C

n-Butyllithium (2.5 M in hexanes, 0.953 mL, 2.38 mmol) was added to a stirred, cooled −78° C. mixture of thiazole (0.169 mL, 2.383 mmol) in THF (5.0 mL) and the mixture was stirred at −78° C. for 15 min. A solution of the dicyclopropylmethanone (250 mg, 2.27 mmol) in THF (3.0 mL) was added dropwise and the mixture was stirred 30 min at −78° C. and then the temperature was allowed to reach room temperature. The reaction was quenched by addition of water and the mixture was extracted with ethyl acetate (3×). The combined organic fractions were washed with brine, dried (Na2SO4), filtered and the solvent was evaporated under reduced pressure. The residue was purified by chromatography on silica gel (0-100% ethyl acetate in hexanes) to give dicyclopropyl(1,3-thiazol-2-yl)methanol (412 mg, 2.110 mmol, 93% yield). MS APCI: [M-OH]+ m/z 179.0.

1. stirringthe mixture was stirred 30 min at −78° C.
2. customto reach room temperature
3. customThe reaction was quenched by addition of water
4. extractionthe mixture was extracted with ethyl acetate (3×)
5. washThe combined organic fractions were washed with brine
6. dry with materialdried (Na2SO4)
7. filtrationfiltered
8. customthe solvent was evaporated under reduced pressure
9. customThe residue was purified by chromatography on silica gel (0-100% ethyl acetate in hexanes)