Sodium hydride → Ethyl 7-acetyl-7-(p-toluoylamino)heptanoate

HRID 1794259Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1794259
[H-].[Na+].[C:3]1([CH3:16])[CH:8]=[CH:7][C:6]([C:9]([NH:11][CH2:12][C:13](=[O:15])[CH3:14])=[O:10])=[CH:5][CH:4]=1.I[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24]>CN(C)C=O>[C:13]([CH:12]([NH:11][C:9]([C:6]1[CH:5]=[CH:4][C:3]([CH3:16])=[CH:8][CH:7]=1)=[O:10])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])(=[O:15])[CH3:14]

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 10880140Ethyl 6-iodohexanoateHCID 218667451-(p-Toluoylamino)-2-propanone

Produkt 1

HCID 21866896Ethyl 7-acetyl-7-(p-toluoylamino)heptanoateAusbeute 65,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel3×

Versuchsvorschrift

A suspension (100 ml) of 60% sodium hydride (2.64 g) in N,N-dimethylformamide was cooled to −18° C. with an ice-sodium chloride bath, and 31 ml of a solution of 12.62 g of 1-(p-toluoylamino)-2-propanone in N,N-dimethylformamide was added dropwise slowly. After 1-hour-stirring, 31 ml of a solution of 16.21 g of ethyl 6-iodohexanoate in N,N-dimethylformamide was added dropwise slowly. The ice-bath was removed and the mixture was stirred for 18 hours at room temperature. After addition of ice-cold water, the reaction solution was extracted with ethyl acetate, washed with water and brine sequentially, dried over anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (Wakogel® C-200, n-hexane:ethyl acetate=3:1) to provide 13.13 g of the objective compound as yellow oil.

Aufarbeitung

  1. customThe ice-bath was removed
  2. stirringthe mixture was stirred for 18 hours at room temperature
  3. additionAfter addition of ice-cold water
  4. extractionthe reaction solution was extracted with ethyl acetate
  5. washwashed with water and brine sequentially
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (Wakogel® C-200, n-hexane:ethyl acetate=3:1)

Quellen und Nachweise

ORD-Eintrag
ord-220b418fa9004a4e94a339620c067a78
Quelldatensatz
uspto-grants-2006_04
Patentnummer
US07022723B2

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