Reacción #1869150

Ecuación de reacción

monoethyl malonate

n-BuLi

10-undecenoyl chloride

→

( 1 )

Rendimiento 98.6%

Ethyl 3-oxo-12-tridecenoate

Rendimiento 98.6%

Disolventes

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONAfter the addition
2. 2
   TemperaturaThe reaction mixture was then re-cooled to −78° C.
3. 3
   Otro30 minutes
4. 4
   Otroat room temperature
5. 5
   OtroThe solvent was removed under reduced pressure
6. 6
   workup.DISSOLUTIONthe residue was re-dissolved in 50 mL ethyl acetate
7. 7
   LavadoThe solution was washed with 1 M HCl (100 mL), saturated aqueous NaHCO3 (50 mL), and brine (50 mL)
8. 8
   SecadoThe organic layer was dried over MgSO4
9. 9
   Concentraciónconcentrated

Procedimiento

A stirred solution of monoethyl malonate (5.3 g, 40 mmol) in anhydrous THF (150 mL) was cooled to −78° C. under an argon atmosphere, and n-BuLi (2.5 M, 32 mL, 80 mmol) was added drop-wise via an air-tight syringe. After the addition, the temperature was raised to 0° C., and the stirring was continued for 1 hour. The reaction mixture was then re-cooled to −78° C., and 10-undecenoyl chloride (25 mmol) was added drop-wise via an air-tight syringe. The mixture was stirred for one hour at −78° C., 30 minutes at 0° C., and 30 minutes at room temperature. The solvent was removed under reduced pressure, and the residue was re-dissolved in 50 mL ethyl acetate. The solution was washed with 1 M HCl (100 mL), saturated aqueous NaHCO3 (50 mL), and brine (50 mL). The organic layer was dried over MgSO4 and concentrated to give (1) (6.270 g). The crude product was used for the next reaction without further purification. 1H NMR (400 MHz, CDCl3) δ 1.28-1.40 (m, 13H), 1.58 (m, 2H), 2.03 (m, 2H), 2.53 (t, J=7 Hz, 2H), 3.43 (s, 2H), 4.21 (q, J=7 Hz, 2H), 4.97 (m, 2H), 5.80 (m, 1H).

Fuente