1-Methoxynaphthalene → HCID 15617937, Verbindung

HRID 703917

Reaktionsgleichung

Reaktionsgleichung von HRID 703917
C([Li])CCC.[CH3:6][O:7][C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[CH:10][CH:9]=1.Br[CH2:19][CH2:20][CH2:21][CH2:22][Cl:23].[Cl-].[NH4+]>C1CCCCC1>[Cl:23][CH2:22][CH2:21][CH2:20][CH2:19][C:9]1[CH:10]=[CH:11][C:12]2[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:8]=1[O:7][CH3:6]

Komponenten

6

Edukt 4

HCID 166681-MethoxynaphthaleneHCID 25517Ammonium ChlorideHCID 813641-Bromo-4-chlorobutaneHCID 178418339Butyllithium

Produkt 1

HCID 15617937HCID 15617937, VerbindungAusbeute 39 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8078CyclohexaneLösungsmittel2×

Versuchsvorschrift

A solution of N,N,N',N'-tetramethylenediamine (18.12 mL, 0.120 mole) in cyclohexane (36 mL) was treated with n-butyllithium (1.55M in hexane; 79.8 mL, 0.123 mole) at room temperature. A solution of 1-methoxynaphthalene (17.4 mL, 0.120 mole) in cyclohexane (20 mL) was added over 30 minutes, and the resulting solution was stirred for 1.5 hours. It was then cooled to 0°, and 1-bromo-4-chlorobutane (27.0 mL, 0.234 mole) was added over 15 minutes. The mixture was warmed to room temperature and stirred for 17 hours, then poured into saturated aqueous ammonium chloride and extracted with ethyl acetate. The crude product was chromatographed with 98:2 hexane/ether to provide the title compound (11.60 g, 39%) as a pale yellow oil.

Aufarbeitung

  1. temperatureIt was then cooled to 0°
  2. stirringstirred for 17 hours
  3. extractionextracted with ethyl acetate
  4. customThe crude product was chromatographed with 98:2 hexane/ether

Quellen und Nachweise

ORD-Eintrag
ord-355c88f0ad1c48f4adbccaf6c649e74a
Quelldatensatz
uspto-grants-1991_01
Patentnummer
US04985435

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