Reaktion #533391

ord-b1571d08fcfd4e0289b13b9841a2c7e7

Reaktionsgleichung

COC(=O)c1ccc2cc(Br)ccc2c1
Methyl 6-bromo-2-naphthoate
CC(C)[CH2][Al+][CH2]C(C)C.[H-]
diisobutyl aluminum hydride
O=C([O-])O.[Na+]
Sodium bicarbonate
OCc1ccc2cc(Br)ccc2c1
solid
Ausbeute 96.0%
OCc1ccc2cc(Br)ccc2c1
(6-bromonaphthalene-2-yl)methanol
Ausbeute 96.0%

Lösungsmittel

Reaktionsbedingungen

Temperatur
0°CELSIUS
Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Sonstigethe solvent was removed by extraction with water and dichloromethane
  2. 2
    SonstigeThe extracted material was dried in vacuum

Vorschrift

Methyl 6-bromo-2-naphthoate (5 g, 18.9 mmol) was dissolved in purified THF (100 mL) under a nitrogen atmosphere, the reaction solution was cooled down to 0° C., and then diisobutyl aluminum hydride (18.9 mL, 1.0M hexane solution) was added thereto. The reaction mixture solution was stirred at room temperature for 3 hours. Sodium bicarbonate (20 mL) was added to the reaction mixture solution, and then the solvent was removed by extraction with water and dichloromethane. The extracted material was dried in vacuum to thereby obtain a white solid (4.3 g, yield: 95%).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08476474B2uspto-grants-2013_07