Acetone → HCID 22392005, compound

Temperature

-50 °C

To a suspension of 2,5-dibromopyridine in toluene (5 ml/mmol) at −78° C., was added n-butyllithium 2.5M in hexanes (1 eq) and the resulting mixture was stirred in the cold for 2.5 hours. Acetone (1 eq) was added, and the mixture was warmed to −50° C. and became a brown solution. After cooling down to −78° C., more n-butyllithium (1 eq) was added along with ether (2 ml/mmol). After stirring in the cold for a further hour, tributyltin chloride (1.1 eq) was added and the mixture was warmed to room temperature and stirred for 2 hours. The mixture was quenched with saturated aqueous ammonium chloride solution and partitioned between ethyl acetate and water. The crude product from the organic phase was chromatographed on silica gel eluting with a 1:9 mixture of ethyl acetate and hexane to afford the 2-(1-hydroxy-1-methylethyl)-5-tributylstannylpyridine compound as a colorless liquid.

1. temperatureAfter cooling down to −78° C.
2. stirringAfter stirring in the cold for a further hour
3. temperaturethe mixture was warmed to room temperature
4. stirringstirred for 2 hours
5. customThe mixture was quenched with saturated aqueous ammonium chloride solution
6. custompartitioned between ethyl acetate and water
7. customThe crude product from the organic phase was chromatographed on silica gel eluting with a 1:9 mixture of ethyl acetate and hexane

ORD record

ord-e1b823fc21374d1d8834b23d87509039

Source dataset

uspto-grants-2004_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06677351B2