Reaction #1869150

Reaction equation

monoethyl malonate

n-BuLi

10-undecenoyl chloride

→

( 1 )

Yield 98.6%

Ethyl 3-oxo-12-tridecenoate

Yield 98.6%

Solvents

THF

Conditions

Workup

1. 1
   workup.ADDITIONAfter the addition
2. 2
   TemperatureThe reaction mixture was then re-cooled to −78° C.
3. 3
   Other30 minutes
4. 4
   Otherat room temperature
5. 5
   OtherThe solvent was removed under reduced pressure
6. 6
   workup.DISSOLUTIONthe residue was re-dissolved in 50 mL ethyl acetate
7. 7
   WashThe solution was washed with 1 M HCl (100 mL), saturated aqueous NaHCO3 (50 mL), and brine (50 mL)
8. 8
   DryingThe organic layer was dried over MgSO4
9. 9
   Concentrationconcentrated

Procedure

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).

Source