cis-1-Ethoxy-2-(tri-n-butylstannyl)ethylene → HCID 15107982, compound

n-BuLi (1.6M in hexanes, 1.52 ml, 2.43 mmol) was added to a solution of cis-1-ethoxy-2-(tri-n-butylstannyl)ethylene (961 mg, 2.66 mmol) in dry THF (7.5 ml) at -78° C. The mixture was stirred for 1 hour, then treated with a solution of 4-(4-fluorophenyl)-2-(1-methylethyl)-6-phenyl-3-pyridinecarboxaldehyde (708 mg, 2.22 mmol) in THF (3.5 ml). One hour after the addition, the reaction was immersed in an ice bath, stirred for 5 minutes, then the mixture was quenched with H2O (8 ml) and 10% HCl (8 ml). The solution was stirred at room temperature for 2 hours, then basicified with 10% NaOH (10 ml) and extracted twice with Et2O. The combined Et2O layers were washed with H2O and brine, dried (Na2 SO4), then filtered and stripped to give a yellow oil. Chromatographic purification of the oil (Flash, Merck SiO2, 10% EtOAc in hexane) gave (E)-3-[4-(4-fluorophenyl)-2-(1-methylethyl)-6-phenyl-3-pyridinyl]-2-propenal (665 mg, 87%) as a white solid. Recrystallization from hot hexane gave analytically pure material (580 mg).

1. additionOne hour after the addition
2. customthe reaction was immersed in an ice bath
3. stirringstirred for 5 minutes
4. customthe mixture was quenched with H2O (8 ml) and 10% HCl (8 ml)
5. stirringThe solution was stirred at room temperature for 2 hours
6. extractionextracted twice with Et2O
7. washThe combined Et2O layers were washed with H2O and brine
8. customdried (Na2 SO4)
9. filtrationfiltered
10. customto give a yellow oil
11. customChromatographic purification of the oil (Flash, Merck SiO2, 10% EtOAc in hexane)

ORD record

ord-1a93f182429d4769ac0b2758b3551d23

Source dataset

uspto-grants-1997_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05691322