3,5-Dimethylisoxazole → HCID 54052374, compound

Temperature

-78 °C

To a solution of 3,5-dimethylisoxazole (9.71 g, 100 mmol) in dry tetrahydrofuran (30 ml) cooled to -78° C. was added n-BuLi (2.5M in hexane, 100 mmol). The reaction mixture was stirred at -78° C. for 1 h. A solution of 3-quinuclidinone (6.25 g, 50 mmol) dissolved in dry tetrahydrofuran (50 ml) was added. The reaction mixture was stirred for 2 h at -78° C., then quenched with water (100 ml) and acidified with concentrated hydrochloric acid. The water phase was extracted with ether (2×50 ml), then basified with solid potassium carbonate and extracted with methylene chloride (4×100 ml). The methylene chloride phases were collected and dried over magnesium sulfate. After evaporation of the solvent the title compound was isolated in 10.04 g. 90% yield.

1. additionwas added
2. stirringThe reaction mixture was stirred for 2 h at -78° C.
3. customquenched with water (100 ml)
4. extractionThe water phase was extracted with ether (2×50 ml)
5. extractionextracted with methylene chloride (4×100 ml)
6. customThe methylene chloride phases were collected
7. dry with materialdried over magnesium sulfate
8. customAfter evaporation of the solvent the title compound
9. customwas isolated in 10.04 g

ORD record

ord-5c29921343d04e0ca254f2a5c5f49e70

Source dataset

uspto-grants-1999_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05859004