Tributyltin Chloride → cis-1-Ethoxy-2-(tri-n-butylstannyl)ethylene

温度

-78 °C

(Ref. Wollenberg, R. H.; Albizati, K. F.; Peries, R. J. Am. Chem. Soc. 1977, 99, 22, 7365-7367.) To a −78° C. solution of (Z)-2-ethoxy-1-bromoethene (5.0 mL, 46.8 mmol) in diethyl ether (160 mL) was added a 1.7 M solution of tert-butyl lithium in pentane (55 mL), dropwise over 20 min. This pale yellow solution was stirred at −78° C. for 40 min, and then chloro-tri-n-butylstannane (13.3 mL, 49.0 mmol) was added, dropwise over 7 minutes. The resulting reaction mixture was allowed to warm slowly. Once the cooling bath had reached −30° C., saturated aq. NaHCO3 (150 mL) was added, and the cooling bath was removed. This mixture was stirred for 15 minutes, and then the layers were separated. The aq. layer was extracted with diethyl ether (2×50 mL). The combined organic layers were dried over Na2SO4, filtered, and concentrated to afford (Z)-2-ethoxy-1-tri-n-butylstannanylethene.

1. customThe resulting reaction mixture
2. temperatureto warm slowly
3. customhad reached −30° C.
4. customthe cooling bath was removed
5. stirringThis mixture was stirred for 15 minutes
6. customthe layers were separated
7. extractionThe aq. layer was extracted with diethyl ether (2×50 mL)
8. dry with materialThe combined organic layers were dried over Na2SO4
9. filtrationfiltered
10. concentrationconcentrated

ORDレコード

ord-ea388c30fc5d41d69b8c89fc5b0633a5

出典データセット

uspto-grants-2010_08

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07767815B2