cis-1-Ethoxy-2-(tri-n-butylstannyl)ethylene → HCID 21471346, compound

Temperature

-78 °C

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 (1.06 gm, 2.94 mmol) in dry THF (7.5 ml) at -78° C. The mixture was stirred for 11/4 hours, then cooled to -100° C. (liquid N2 /methanol) and treated with a solution of 4-(4-fluorophenyl)-2-methyl-6-phenyl-3-pyridinecarboxaldehyde (707 mg, 2.43 mmol) in THF (3.0 ml). Forty-five minutes after the addition, the temperature was raised to -78° C. and the mixture was stirred for an additional 50 minutes. The solution was then stirred in an ice bath for 5 minutes and subsequently quenched with H2O (8 ml) and 10% HCl (8 ml). After stirring at room temperature for 1.5 hours, the mixture was made basic with 10% NaOH (10 ml) and extracted twice with Et2O. The combined Et2O layers were washed with H2O and brine, dried (Na2SO4), filtered and stripped to yield a solid. The solid was washed with cold Et2O. The Et2O washings were stripped and triturated with cold hexane to give additional solid, which was pooled with the above solid to give 586 mg (76%) (E)-3-[4-(4-fluorophenyl)-2-methyl-6-phenyl-3-pyridinyl]-2-propenal. Analytically pure material was obtained by recrystallization from hot hexane/EtOAc.

1. additionForty-five minutes after the addition
2. stirringthe mixture was stirred for an additional 50 minutes
3. stirringThe solution was then stirred in an ice bath for 5 minutes
4. customsubsequently quenched with H2O (8 ml) and 10% HCl (8 ml)
5. stirringAfter stirring at room temperature for 1.5 hours
6. extractionextracted twice with Et2O
7. washThe combined Et2O layers were washed with H2O and brine
8. dry with materialdried (Na2SO4)
9. filtrationfiltered
10. customto yield a solid
11. washThe solid was washed with cold Et2O
12. customtriturated with cold hexane
13. customto give additional solid, which

ORD record

ord-023f03c1057a4c7dafa5aa79250795ff

Source dataset

uspto-grants-1996_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05506219