Reacción #1994250

Ecuación de reacción

LDA

2,4-pentanedione

Allyl bromide

→

7-octene 2,4-pentanedione

Rendimiento 22.0%

Disolventes

THF

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONAfter addition
2. 2
   OtroAfter removing of ice-water bath
3. 3
   Otrothe resulting reaction
4. 4
   workup.STIRRINGto stir for 20 min at room temperature
5. 5
   Otrobefore being quenched by saturated aqueous 1 M of HCl (aq)
6. 6
   ExtracciónThe reaction mixture was extracted with EtOAc (2×50 mL)
7. 7
   LavadoThe combined EtOAc extracts were washed with brine, water (3×50 mL)
8. 8
   Secadodried over MgSO4
9. 9
   FiltraciónAfter filtration
10. 10
    Concentraciónthe solution was concentrated
11. 11
    Otrothe residue was purified by chromatography
12. 12
    OtroThe product, 3, was isolated as a pale yellow oil, 1.21 g (22% yield)

Procedimiento

2,4-pentanedione (4.11 mL, 39.9 mmol) was dissolved in anhydrous THF (120 mL) and cooled to 0° C. using an ice-water bath. To the stirred THF solution, 2.2 equivalent of 2.0 M LDA (44 mL, 87.8 mmol) was slowly added. After addition was complete, the mixture was stirred at 0° C. for 20 min under argon atmosphere. Allyl bromide (3.46 mL, 39.9 mmol) was then added to the resulting pale red solution at 0° C. under argon. After removing of ice-water bath, the resulting reaction was allowed to stir for 20 min at room temperature before being quenched by saturated aqueous 1 M of HCl (aq). The reaction mixture was extracted with EtOAc (2×50 mL). The combined EtOAc extracts were washed with brine, water (3×50 mL), dried over MgSO4. After filtration, the solution was concentrated, and the residue was purified by chromatography using 9:1 ratio of n-hexane:EtOAc. The product, 3, was isolated as a pale yellow oil, 1.21 g (22% yield).

Fuente