Hexane → HCID 12069883, compound

Isopropyltriphenylphosphonium iodide (1.18 g; 2.73 mmol) was added to benzene (35 ml). While the mixture was stirred under nitrogen atmosphere at room temperature, n-butyl lithium in n-hexane (1.56 M: 1.8 ml; 2.73 mmol) was added dropwise. The mixture was stirred for 10 minutes, and Compound 8 (0.49 g; 1.82 mmol) in benzene (35 ml) was added dropwise thereto, followed by stirring for 3 hours at room temperature. Reaction was stopped by pouring the mixture into ice/water, followed by extraction with benzene (100 ml). The organic layer was washed with saturated aqueous sodium bicarbonate solution and with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=20:1), to thereby yield 0.13 g of the target compound as pale yellow oily matter (yield: 24.2%).

1. stirringThe mixture was stirred for 10 minutes
2. stirringby stirring for 3 hours at room temperature
3. customReaction
4. extractionfollowed by extraction with benzene (100 ml)
5. washThe organic layer was washed with saturated aqueous sodium bicarbonate solution and with saturated brine
6. dry with materialdried over anhydrous sodium sulfate
7. customThe solvent was evaporated under reduced pressure
8. customthe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=20:1)

ORD record

ord-b94d84fdc09a44068dbd86cb3d7baa0f

Source dataset

uspto-grants-2003_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06586633B1