Tributylstannane → 2-Cyclopenten-1-one, 3-(tributylstannyl)-

Temperature

0 °C

3-Ethoxy-cyclopent-2-enone (1.0 g, 7.9 mmol) was dissolved in THF (2 ml) and was placed in an addition funnel atop a flask equipped with stirring and a cooling bath. The flask was charged with THF (10 ml) and diisopropylamine (0.88 g, 8.7 mmol) and cooled to 0° C. To the solution was added n-butyllithium (1.9M, 4.6 ml) and the resulting solution stirred for five minutes. While still at 0° C., tributyltinhydride (2.35 ml, 8.7 mmol) was added to give a yellow solution, then after 15 minutes at 0° C., the solution was cooled to -70° C. At -70° C. the 3-ethoxy-cyclopent-2-enone was added dropwise, and after addition was complete, the reaction was stirred at -20° for one hour. The cooling bath was removed and the reaction quenched with NH4Cl solution and diluted with ether. The organic layer was separated, dried (MgSO4), filtered, and evaporated to give an oil. Chromatography on silica gel with CH2Cl2 gave the title compound (1.8 g).

1. customwas placed in an addition funnel atop a flask
2. customequipped
3. stirringthe resulting solution stirred for five minutes
4. customto give a yellow solution
5. temperaturethe solution was cooled to -70° C
6. additionafter addition
7. stirringthe reaction was stirred at -20° for one hour
8. customThe cooling bath was removed
9. customthe reaction quenched with NH4Cl solution
10. additiondiluted with ether
11. customThe organic layer was separated
12. dry with materialdried (MgSO4)
13. filtrationfiltered
14. customevaporated
15. customto give an oil

ORD record

ord-5f784cc3494541a7b4067950586d7e60

Source dataset

uspto-grants-1990_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04945160