Sodium Iodide → Ethyl 3-(4-methylphenyl)-3-oxo-2-(allyl)propanoate

HRID 466420노트

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HRID 466420 반응식
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:15])[CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][CH:3]=1.[O-]CC.[Na+].[CH2:20](Br)[CH:21]=[CH2:22].[I-].[Na+]>>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8](=[O:15])[CH:9]([CH2:22][CH:21]=[CH2:20])[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:6][CH:7]=1

참가 물질

5

반응물 4

HCID 5238Sodium IodideHCID 7841Allyl bromideHCID 292637Ethyl 3-(4-methylphenyl)-3-oxopropanoateHCID 2723922Sodium ethoxide

생성물 1

HCID 15698113Ethyl 3-(4-methylphenyl)-3-oxo-2-(allyl)propanoate수율 97.5%

실험 절차

Ethyl 3-(4-methylphenyl)-3-oxopropanoate (prepared as described in W. Wierenga and H. I. Skulnick, J. Org. Chem. (1979), 44, 310) (63.66 g, 309 mmol, 1 eq) was added to a freshly prepared sodium ethoxide solution (Na, 7.43 g, 323 mmol, 1.05 eq; EtOH, 250 mL). The ethanol was removed in vacuo and the residue was dissolved in DMF (250 mL). Allyl bromide (29.3 mL, 338 mmol, 1.1 eq) followed by sodium iodide (4.56 g, 304 mmol, 1 eq) were then added and the contents stirred overnight at room temperature. The DMF was removed in vacuo, water (250 mL) was added and the aqueous layer extracted with ethyl acetate (3×200 mL). The organic layers were dried (MgSO4) and the solvent removed in vacuo to yield 74.21 g of an amber oil. NMR (200 MHz, CDCl3) δ 7.81 (d, 2H, J=10 Hz); 7.30 (d, 2H, J=10 Hz); 5.96-5.72 (m, 1H); 5.21-5.00 (m, 2H); 4.41 (t, 1H, J=7 Hz); 4.16 (q, 2H, J=7 Hz); 2.78 (t, 2H, J=7 Hz); 2.42 (s, 3H); 1.18 (t, 3H, J=7 Hz). Anal. Calcd. for C15H18O3 : C, 73.15; H, 7.37. Found: C, 73.10; H, 7.38.

후처리

  1. customThe ethanol was removed in vacuo
  2. dissolutionthe residue was dissolved in DMF (250 mL)
  3. additionwere then added
  4. customThe DMF was removed in vacuo, water (250 mL)
  5. additionwas added
  6. extractionthe aqueous layer extracted with ethyl acetate (3×200 mL)
  7. dry with materialThe organic layers were dried (MgSO4)
  8. customthe solvent removed in vacuo

출처 및 근거

ORD 기록
ord-58c2283e7bc24845bb7e8f881992aae1
출처 데이터셋
uspto-grants-1992_10
특허 번호
US05155118

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