Water → 2, 3-Dimethoxybenzyl-n-pentylmalonic acid diethyl ester

HRID 1756765

Reaktionsgleichung

Reaktionsgleichung von HRID 1756765
[H-].[Na+].[CH2:3]([O:5][C:6](=[O:18])[CH:7]([CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH3:4].[CH3:19][O:20][C:21]1[C:28]([O:29][CH3:30])=[CH:27][CH:26]=[CH:25][C:22]=1[CH2:23]Cl.O>CN(C)C=O>[CH2:3]([O:5][C:6](=[O:18])[C:7]([CH2:23][C:22]1[CH:25]=[CH:26][CH:27]=[C:28]([O:29][CH3:30])[C:21]=1[O:20][CH3:19])([CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH3:4]

Komponenten

6

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 80167Diethyl pentylmalonateHCID 27583941-(Chloromethyl)-2,3-dimethoxybenzene

Produkt 1

HCID 540695252, 3-Dimethoxybenzyl-n-pentylmalonic acid diethyl esterAusbeute 73,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel3×

Versuchsvorschrift

To a suspension of 60% sodium hydride (440 mg, 11 mmol) in 5 ml of dimethylformamide was added a solution of 2.30 g (10 mmol) of n-pentylmalonic acid diethyl ester in 5 m of dimethylformamide under stirring and ice cooling, and the resultant mixture was stirred for 30 minutes. A solution of 1.86 g (10 mmol) of 2, 3-dimethoxybenzyl chloride in 5 ml of dimethylformamide was dropwise added to the mixture, which was stirred at 70° C. for 1 hour. After cooling, the reaction mixture was mixed with water and extracted with ethyl acetate. The organic layers were combined, washed with water and saturated saline in this order, dried over anhydrous magnesium sulfate and the solvent evaporated in vacuo. The residue was chromatographed on a silica gel column, eluting with ethyl acetate/hexane (1/12) to give 2.78 g of 2, 3-dimethoxybenzyl-n-pentylmalonic acid diethyl ester as a colorless oil. Yield, 73%.

Aufarbeitung

  1. stirringwas stirred at 70° C. for 1 hour
  2. temperatureAfter cooling
  3. extractionextracted with ethyl acetate
  4. washwashed with water and saturated saline in this order
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent evaporated in vacuo
  7. customThe residue was chromatographed on a silica gel column
  8. washeluting with ethyl acetate/hexane (1/12)

Quellen und Nachweise

ORD-Eintrag
ord-c46aebd1d2a04dbe9019a4ac1edbddb4
Quelldatensatz
uspto-grants-1995_08
Patentnummer
US05442060

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