Reaktion #336245

Reaktionsgleichung

water

magnesium

methyl 6-bromo-2-naphthoate

→

2-naphthoic acid

Lösungsmittel

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONOnce the addition
2. 2
   Temperaturthe mixture is heated
3. 3
   Temperaturat reflux for 2 hours at which point the temperature of the mixture
4. 4
   Sonstigeto return to ambient temperature
5. 5
   workup.ADDITIONare added
6. 6
   Extraktionextracted with CH2Cl2
7. 7
   Sonstigedried
8. 8
   Sonstigeevaporated
9. 9
   SonstigeThe residue is chromatographed on a silica column (eluant
10. 10
    workup.ADDITIONmixture of heptane (70%) and ether (30%)

Vorschrift

33.3 g (79 mmol) of the compound produced in part (a) above, dissolved in 200 ml of THF are slowly added to a suspension of magnesium (2.9 g, 118 Atg) in 60 ml of THF. Once the addition is complete, the mixture is heated at reflux for 2 hours at which point the temperature of the mixture is permitted to return to ambient temperature. 10.8 g (79 mmol) of anhydrous zinc chloride are added and the mixture is stirred for one hour at ambient temperature, at which point 10.5 g (39.5 mmol) of methyl 6-bromo-2-naphthoate and 500 mg of NiCl2 /DPPE complex are added. This mixture is then stirred for 2 hours at ambient temperature, poured into water, extracted with CH2Cl2, dried and evaporated. The residue is chromatographed on a silica column (eluant: mixture of heptane (70%) and ether (30%). 18.5 (90%) of the methyl ester of 6-[3-(1-adamantyl)-4 ™tert.butyldimethylsilyloxyphenyl]-2-naphthoic acid are obtained. Melting point: 152°-153° C.

Quelle