Acetone → 2-Thiazol-2-yl-propan-2-ol

Temperature

-20 °C

2-Bromothiazole (12.00 g, 73.2 mmol) was taken up in THF (150 mL) and cooled to −20° C. Isopropylmagnesium chloride (2.0 M in THF, 38.4 mL, 77 mmol) was added dropwise. After stirring for 1 h (−10° C. to 0° C.), the reaction was cooled to back −20° C., and acetone (5.10 g, 88 mmol) was added dropwise. The reaction was stirred for 30 min at −20° C. then warmed to room temperature. After 2 h at room temperature, the reaction was quenched with saturated NH4Cl and extracted with ethyl acetate (2×). The combined organic layers were washed with brine, dried (MgSO4), and evaporated. The residue was purified by flash chromatography (0-50% ethyl acetate in hexanes) to afford 8.97 g (86%) of 2-(1,3-thiazol-2-yl)propan-2-ol as a pale yellow low-melting solid. MS ESI: [M+H]+ m/z 144.0.

1. temperaturethe reaction was cooled
2. customto back −20° C.
3. stirringThe reaction was stirred for 30 min at −20° C.
4. temperaturethen warmed to room temperature
5. waitAfter 2 h at room temperature
6. customthe reaction was quenched with saturated NH4Cl
7. extractionextracted with ethyl acetate (2×)
8. washThe combined organic layers were washed with brine
9. dry with materialdried (MgSO4)
10. customevaporated
11. customThe residue was purified by flash chromatography (0-50% ethyl acetate in hexanes)

ORD record

ord-df9bac560af149429d901b830ebcc699

Source dataset

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08551984B2