반응 #1869150

반응 방정식

monoethyl malonate

n-BuLi

10-undecenoyl chloride

→

( 1 )

수율 98.6%

Ethyl 3-oxo-12-tridecenoate

수율 98.6%

용매

THF

반응 조건

후처리

1. 1
   workup.ADDITIONAfter the addition
2. 2
   온도The reaction mixture was then re-cooled to −78° C.
3. 3
   기타30 minutes
4. 4
   기타at room temperature
5. 5
   기타The solvent was removed under reduced pressure
6. 6
   workup.DISSOLUTIONthe residue was re-dissolved in 50 mL ethyl acetate
7. 7
   세척The solution was washed with 1 M HCl (100 mL), saturated aqueous NaHCO3 (50 mL), and brine (50 mL)
8. 8
   건조The organic layer was dried over MgSO4
9. 9
   농축concentrated

실험 절차

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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