4-Isopropylaniline → 4-Isopropyl-N-(2,2-diethoxyethyl)aniline

HRID 610049

Reaktionsgleichung

Reaktionsgleichung von HRID 610049
[CH:1]([C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[CH2:11]([O:13][CH:14]([O:17][CH2:18][CH3:19])[CH2:15]Br)[CH3:12].C(=O)(O)[O-].[Na+]>C(O)C>[CH:1]([C:4]1[CH:10]=[CH:9][C:7]([NH:8][CH2:15][CH:14]([O:17][CH2:18][CH3:19])[O:13][CH2:11][CH3:12])=[CH:6][CH:5]=1)([CH3:3])[CH3:2]

Komponenten

5

Edukt 3

HCID 74644-IsopropylanilineHCID 74852Ethane, 2-bromo-1,1-diethoxy-HCID 516892Sodium Bicarbonate

Produkt 1

HCID 196009444-Isopropyl-N-(2,2-diethoxyethyl)anilineAusbeute 90,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of 4-isopropylaniline (7.6 mL, 56 mmol), 2-bromoacetaldehyde diethyl acetal (5.5 mL, 36 mmol) and sodium bicarbonate (4.8 g, 57 mmol) in ethanol (60 mL) was stirred at reflux for 3 days under argon. After cooling to room temperature, the ethanol was removed in vacuo and the product was partitioned between ether and water, washed sequentially with water and brine, and dried over sodium sulfate. After removal of the solvent in vacuo, flash chromatography (silica, 10% ethyl acetate in hexanes) yielded 4-isopropyl-N-(2,2-diethoxyethyl) aniline (8.23 g, 90%).

Aufarbeitung

  1. temperatureat reflux for 3 days under argon
  2. customthe ethanol was removed in vacuo
  3. customthe product was partitioned between ether and water
  4. washwashed sequentially with water and brine
  5. dry with materialdried over sodium sulfate
  6. customAfter removal of the solvent in vacuo, flash chromatography (silica, 10% ethyl acetate in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-4bc69996890742b593cb12a4b60e9adc
Quelldatensatz
uspto-grants-1999_12
Patentnummer
US05998462

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