Lithium tri-s-butylborohydride → 5-Bromo-1-methoxy-3-methyl-8-(1-methylethoxy)naphthalene

HRID 963638Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 963638
[Br:1][C:2]1[C:11]2[C:6](=[C:7]([O:14][CH3:15])[CH:8]=[C:9]([CH2:12]Br)[CH:10]=2)[C:5]([O:16][CH:17]([CH3:19])[CH3:18])=[CH:4][CH:3]=1.CCC(C)[BH-](C(C)CC)C(C)CC.[Li+]>ClCCl>[Br:1][C:2]1[C:11]2[C:6](=[C:7]([O:14][CH3:15])[CH:8]=[C:9]([CH3:12])[CH:10]=2)[C:5]([O:16][CH:17]([CH3:19])[CH3:18])=[CH:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 3611392Lithium tri-s-butylborohydride2×HCID 15341856HCID 15341856, Verbindung

Produkt 1

HCID 110559695-Bromo-1-methoxy-3-methyl-8-(1-methylethoxy)naphthaleneAusbeute 98 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a 0° C. cold solution of 7.60 g (19.6 mmol) 1-bromo-7-bromomethyl-4-isopropoxy-5-methoxy-naphthalene in 150 mL dry dichloromethane, 20.0 mL (20.0 mmol) of a 1M L-selectride-solution was added under Ar. After 2 h, further 2.50 mL (2.50 mmol) 1M L-selectride-solution was added. After that the solvent was removed in vacuo and the residue was filtered over a short silica gel column (petroleum/acetone, 30:1). After removal of the solvent in vacuo, the residue was recrystallized from acetone to give 5.90 g (98%) of 4 as colorless needles (m.p. 78° C.).

Aufarbeitung

  1. customAfter that the solvent was removed in vacuo
  2. filtrationthe residue was filtered over a short silica gel column (petroleum/acetone, 30:1)
  3. customAfter removal of the solvent in vacuo
  4. customthe residue was recrystallized from acetone

Quellen und Nachweise

ORD-Eintrag
ord-9b7a4952e384441b9da5e31d3ce5a314
Quelldatensatz
uspto-grants-1998_06
Patentnummer
US05763613

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