Tributyltin Chloride → HCID 67003585, compound

Temperature

-78 °C

To a cold (−78° C.) solution of the 2-(1-(methoxymethoxy)cyclobutyl)thiazole (Example 1B) (5.67 g, 28.5 mmol) in tetrahydrofuran (95 mL) was added a solution of lithium diisopropylamide (34.1 mmol) in tetrahydrofuran (30 mL) dropwise. The solution was stirred at −78° C. for 45 minutes, and tributyltin chloride (9.26 mL, 34.1 mmol) was added dropwise. The cold bath was removed, and the reaction warmed to room temperature. The ambient reaction was then quenched by the addition of saturated aqueous ammonium chloride solution and ether. The layers were separated, and the aqueous layer was extracted with additional ether. The combined organics were washed with water, dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give the title compound, which was used without further purification. MS ESI(+) m/z 490 [M+H]+.

1. customThe cold bath was removed
2. temperaturethe reaction warmed to room temperature
3. customThe ambient reaction
4. customwas then quenched by the addition of saturated aqueous ammonium chloride solution and ether
5. customThe layers were separated
6. extractionthe aqueous layer was extracted with additional ether
7. washThe combined organics were washed with water
8. dry with materialdried with anhydrous sodium sulfate
9. filtrationfiltered
10. concentrationconcentrated under reduced pressure

ORD record

ord-5a5e4b46560c40618cc23739b276d6e8

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08691810B2