Methyl iodide → Tert-butyl 2-methyl-2-(1,3-thiazol-2-yl)propanoate

Temperatur

0 °C

Toluene (30 mL) was placed in a nitrogen-flushed flask and degassed with nitrogen (20 min). 2-Chlorothiazole (900 mg, 7.53 mmol) and tert-butyl propionate (1.176 g, 9.03 mmol) were added, and the mixture was cooled to 0° C. NaHMDS (0.6 M in toluene, 30.1 mL, 18.06 mmol) was added. The reaction was stirred for 2 h at 0° C., allowed to warm to room temperature, and stirred for 18 h at room temperature. Methyl iodide (3.85 g, 27.1 mmol) was then added. After 1 h at room temperature, the orange reaction was quenched (under nitrogen) with aqueous saturated NH4Cl. The mixture was extracted with ethyl acetate (2×), and the combined organic layers were washed with brine, dried (Na2SO4), filtered and evaporated. Flash chromatography (0-25% ethyl acetate in hexanes) afforded tert-butyl 2-methyl-2-(1,3-thiazol-2-yl)propanoate (1.06 g, 62%) as a pale yellow oil. MS ESI: [M+H]+ m/z 228.1.

1. customflushed flask
2. customdegassed with nitrogen (20 min)
3. temperatureto warm to room temperature
4. stirringstirred for 18 h at room temperature
5. waitAfter 1 h at room temperature
6. customthe orange reaction
7. customwas quenched (under nitrogen) with aqueous saturated NH4Cl
8. extractionThe mixture was extracted with ethyl acetate (2×)
9. washthe combined organic layers were washed with brine
10. dry with materialdried (Na2SO4)
11. filtrationfiltered
12. customevaporated

ORD-Eintrag

ord-bb82558b31444071a7821cc07a9db13c

Quelldatensatz

uspto-grants-2014_06

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08759366B2