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Triethylamine → N,N-dimethylamino acetic acid, 2,3-diethyl-4-methoxynaphth-1-yl ester

HRID 649047
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 649047
C(N(CC)CC)C.[CH2:8]([C:10]1[C:19]([CH2:20][CH3:21])=[C:18]([O:22][CH3:23])[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]=1O)[CH3:9].Cl.[CH3:26][N:27]([CH2:29][C:30]([OH:32])=[O:31])[CH3:28]>C(Cl)Cl>[CH3:26][N:27]([CH2:29][C:30]([O:32][C:11]1[C:12]2[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:18]([O:22][CH3:23])=[C:19]([CH2:20][CH3:21])[C:10]=1[CH2:8][CH3:9])=[O:31])[CH3:28]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 75605N,N-Dimethylglycine hydrochlorideHCID 126649942,3-Diethyl-4-methoxynaphthol

Produkt 1

HCID 23161585N,N-dimethylamino acetic acid, 2,3-diethyl-4-methoxynaphth-1-yl esterAusbeute 72,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

Triethylamine (3 eq) and dry methylene chloride (150 ml) are introduced to a mixture of 2,3-diethyl-4-methoxynaphthol (1.59 g, 6.5 mmole), dimethylamino acetic acid hydrochloride (2 eq, 1.8 g, 13.0 mmole), dicyclohexylcarbadiimide (2 eq, 2.7 g, 13.0 mmole) and 4-dimethylaminpyridine (1 eq, 2.7 ml, 19.5 mmole), prepared under an argon atmosphere, at room temperature under argon. The resulting suspension is stirred at room temperature for 20 hours under argon, then diluted with 300 ml of methylene chloride. The methylene chloride extracts are washed thoroughly with saturated aqueous sodium bicarbonate solution and water, dried over anhydrous magnesium sulfate, filtered and concentrated. The residue is chromatographed through a silica gel (200 g) flash column and eluted by ether to give 1.48 g (72.2%) of N,N-dimethylamino acetic acid, 2,3-diethyl-4-methoxynaphth-1-yl ester as a yellowish brown oil.

Aufarbeitung

  1. customprepared under an argon atmosphere, at room temperature under argon
  2. washThe methylene chloride extracts are washed thoroughly with saturated aqueous sodium bicarbonate solution and water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue is chromatographed through a silica gel (200 g) flash column
  7. washeluted by ether

Quellen und Nachweise

ORD-Eintrag
ord-9325f36e28e24f3892c439f8942e9309
Quelldatensatz
uspto-grants-1988_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04737519

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