Реакция #1869150

Уравнение реакции

monoethyl malonate

n-BuLi

10-undecenoyl chloride

→

( 1 )

Выход 98.6%

Ethyl 3-oxo-12-tridecenoate

Выход 98.6%

Растворители

THF

Условия реакции

Обработка

1. 1
   workup.ADDITIONAfter the addition
2. 2
   ТемператураThe reaction mixture was then re-cooled to −78° C.
3. 3
   Другое30 minutes
4. 4
   Другоеat room temperature
5. 5
   ДругоеThe solvent was removed under reduced pressure
6. 6
   workup.DISSOLUTIONthe residue was re-dissolved in 50 mL ethyl acetate
7. 7
   ПромывкаThe solution was washed with 1 M HCl (100 mL), saturated aqueous NaHCO3 (50 mL), and brine (50 mL)
8. 8
   СушкаThe organic layer was dried over MgSO4
9. 9
   Концентрированиеconcentrated

Методика

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).

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