Potassium bis(trimethylsilyl)amide → HCID 53833984, compound

To a solution of trimethylphosphonoacetate (12.34 g ; 61.6 mmol) in 500 mL of THF cooled to -78° C. under nitrogen with stirring, 136 mL (61.6 mmol) of 0.5M potassium bis(trimethylsilyl)amide was added dropwise over a 1/2 h period. The reaction mixture was stirred continuously at -78° C. for 1 hr. To the mixture was added 8.5 g (61.6 mmol) of 5-propyl-2-furancarboxaldehyde and 3 mL of THF over a 10 min period with stirring. After 1 h, stirring was stopped and the reaction mixture was allowed to warm to room temperature over a 2 h period. The reaction mixture was quenched with an aqueous solution of saturated ammonium chloride with stirring, and water was added to dissolve the precipitated salts into solution. The THF/agueous solution was washed with ether (200 mL), and the aqueous layer was washed again with 100 mL of ether. The combined organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo to yield 10.95 g (87.9%) of methyl 3-(5-propyl-2-furanyl)prop-2-enoate.

1. stirringThe reaction mixture was stirred continuously at -78° C. for 1 hr
2. stirringwith stirring
3. stirringstirring
4. customThe reaction mixture was quenched with an aqueous solution of saturated ammonium chloride
5. stirringwith stirring
6. additionwater was added
7. dissolutionto dissolve the precipitated salts into solution
8. washThe THF/agueous solution was washed with ether (200 mL)
9. washthe aqueous layer was washed again with 100 mL of ether
10. washThe combined organic layer was washed with brine
11. dry with materialdried over anhydrous magnesium sulfate
12. filtrationfiltered
13. concentrationconcentrated in vacuo

ORD record

ord-cbd0f490f7ab45f384c0976cbdc34b67

Source dataset

uspto-grants-1997_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05665763