Sodium hydride → Ethyl 2-[(4-iodophenyl)methyl]-3-oxoheptanoate

HRID 1110052Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1110052
[O:1]=[C:2]([CH2:9][CH2:10][CH2:11][CH3:12])[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].[H-].[Na+].Br[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([I:23])=[CH:19][CH:18]=1>CS(C)=O>[I:23][C:20]1[CH:21]=[CH:22][C:17]([CH2:16][CH:3]([C:2](=[O:1])[CH2:9][CH2:10][CH2:11][CH3:12])[C:4]([O:6][CH2:7][CH3:8])=[O:5])=[CH:18][CH:19]=1

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 559036Ethyl 3-oxoheptanoateHCID 9542584-Iodobenzyl bromide

Produkt 1

HCID 19018799Ethyl 2-[(4-iodophenyl)methyl]-3-oxoheptanoateAusbeute 29 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

To a solution of 3.77 g (43.8 mmol) ethyl 3-oxoheptanoate in 200 mL DMSO was added 1.75 g (43.8 mmol) 65% NaH in oil. After 10 minutes, 6.5 g (21.9 mmol) α-bromo-4-iodotoluene was added. The mixture was allowed to stir for 2 hours. It was then poured into an ice/brine mixture and extracted 3 times with ether. The combined organic material was washed with brine, dried over MgSO4,stripped of solvent in vacuo, then Still flash chromatographed in 40% CH2Cl2 /hexane to give 2.46 g of the title compound, 29% yield. Rf 0.23 in 40% CH2Cl2 /hexane, visualized by UV and ninhydrin stain; 1H-NMR (300 MHz, CDCl3): δ 7.58 (m,2H), 6.93 (m, 2H), 4.14 (m,2H), 3.72 (3 line m, 1H), 3.09 (m, 2H), 2.44 (12 line m, 2H), 1.50 (m, 2H), 1.22 (m, 2H), 1.21 (3 line m, 3H), 0.86 (3 line m, 3H).

Aufarbeitung

  1. extractionextracted 3 times with ether
  2. washThe combined organic material was washed with brine
  3. dry with materialdried over MgSO4,stripped of solvent in vacuo
  4. customStill flash chromatographed in 40% CH2Cl2 /hexane

Quellen und Nachweise

ORD-Eintrag
ord-ec86c45bdb5b489991c21a6c6d5474e5
Quelldatensatz
uspto-grants-1994_06
Patentnummer
US05324729

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