Chloromethyl Methyl Ether → HCID 18979130, Verbindung

HRID 2393179Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2393179
[N+:1]([C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[CH:6][C:5]=1[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]([OH:22])=[O:21])([O-])=O.C(N(CC)CC)C.[CH3:30][O:31][CH2:32]Cl>CN(C=O)C.C(=O)([O-])O.[Na+]>[NH2:1][C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[CH:6][C:5]=1[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]([O:22][CH2:30][O:31][CH3:32])=[O:21]

Komponenten

6

Edukt 3

HCID 7864Chloromethyl Methyl EtherHCID 8471TriethylamineHCID 18979200HCID 18979200, Verbindung

Produkt 1

HCID 18979130HCID 18979130, VerbindungAusbeute 100,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 516892Sodium BicarbonateLösungsmittel

Versuchsvorschrift

7-(1-Nitro-2-naphthyl)heptanoic acid (2 g) and triethylamine (2.02 g) were dissolved in DMF (10 ml) followed by addition of chloromethyl methyl ether (0.802 g), and the mixture was stirred at room temperature for 20 hours. This reaction mixture was diluted with cold saturated aqueous sodium hydrogen carbonate solution and extracted with ethyl acetate. The organic layer was washed with water, dried, and concentrated to dryness. Using the residue, 10% palladium-on-carbon (0.23 g), and ethanol (23 ml), a catalytic hydrogenation reaction was carried out at atmospheric temperature and pressure for 18 hours. The catalyst was then filtered off and the filtrate was concentrated under reduced pressure to provide methoxymethyl 7-(1-amino-2-naphthyl)heptanoate (2.1 g).

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. customdried
  4. concentrationconcentrated to dryness
  5. customa catalytic hydrogenation reaction
  6. waitwas carried out at atmospheric temperature and pressure for 18 hours
  7. filtrationThe catalyst was then filtered off
  8. concentrationthe filtrate was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-5092ef94a8184bd4b67b4a41162f1c0e
Quelldatensatz
uspto-grants-1998_09
Patentnummer
US05804601

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