Oxazole → HCID 22293929, compound

Temperature

0 °C

To a solution of oxazole (2.93 g, 42.5 mmol) in tetrahydrofuran (150 ml) at −70° C. under a nitrogen atmosphere was added n-butyllithium (17 ml of a 2.5M solution in hexanes) dropwise and the solution stirred for 20 minutes. Zinc chloride (84.9 ml of a 1M solution in diethyl ether) was added and the solution warmed to 0° C. over 45 minutes. Solid cuprous iodide (8.09 g, 42.5 mmol) was added and after 10 minutes, 3-chloropropionyl chloride (8.38 ml, 87.8 mmol) was added. After 1 h, ethyl acetate and aqueous ammonium chloride solution were added. The organic layer was separated and washed sequentially with aqueous ammonium chloride solution, water and brine. The solution was dried (sodium sulphate) and evaporated to yield 15.5 g of the crude product as a red oil. This mixture was used without further purification.

1. waitAfter 1 h
2. customThe organic layer was separated
3. washwashed sequentially with aqueous ammonium chloride solution, water and brine
4. dry with materialThe solution was dried (sodium sulphate)
5. customevaporated

ORD record

ord-15844cb6198141a2b62a690f49031608

Source dataset

uspto-grants-2005_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06887871B2