Reaktion #1869151

Reaktionsgleichung

monoethyl malonate

n-BuLi

decanoyl chloride

→

ethyl 3-oxododecanoate

Ausbeute 120.2%

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONAfter the addition
2. 2
   TemperaturThe mixture was then re-cooled to −78° C.
3. 3
   SonstigeThe solvent was removed under reduced pressure
4. 4
   workup.DISSOLUTIONthe residue was re-dissolved in 50 mL ethyl acetate
5. 5
   WaschenThe solution was washed with 1 M HCl (100 mL), saturated aqueous NaHCO3 (50 mL), and brine (50 mL)
6. 6
   TrocknenThe organic layer was dried over MgSO4
7. 7
   Einengenconcentrated

Vorschrift

A stirred solution of monoethyl malonate (1.26 g, 9.6 mmol) in 25 mL anhydrous THF was cooled to −78° C. under an argon atmosphere, and n-BuLi (2.5 M, 8 mL, 20 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 mixture was then re-cooled to −78° C., and decanoyl chloride (1.044 mL, 5 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 ethyl 3-oxododecanoate (1.456 g). The crude product was used for the next reaction. 1H NMR (500 MHz, CDCl3) δ 0.88 (t, J=7 Hz, 3H), 1.20-1.38 (m, 12H), 1.50-1.68 (m, 2H), 2.53 (t, J=7.5 Hz, 2H), 3.43 (s, 2H), 4.20 (q, J=7 Hz, 2H); 13C NMR (125 MHz, CDCl3) δ 13.975, 13.988, 22.5, 23.4, 28.91, 29.14, 29.26, 29.29, 31.8, 42.9, 49.2, 61.2, 167.2, 202.9.

Quelle