反応 #1869150

反応方程式

monoethyl malonate

n-BuLi

10-undecenoyl chloride

→

( 1 )

収率 98.6%

Ethyl 3-oxo-12-tridecenoate

収率 98.6%

溶媒

THF

反応条件

後処理

1. 1
   workup.ADDITIONAfter the addition
2. 2
   温度The reaction mixture was then re-cooled to −78° C.
3. 3
   その他30 minutes
4. 4
   その他at room temperature
5. 5
   その他The solvent was removed under reduced pressure
6. 6
   workup.DISSOLUTIONthe residue was re-dissolved in 50 mL ethyl acetate
7. 7
   洗浄The solution was washed with 1 M HCl (100 mL), saturated aqueous NaHCO3 (50 mL), and brine (50 mL)
8. 8
   乾燥The organic layer was dried over MgSO4
9. 9
   濃縮concentrated

実験手順

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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