Reaktion #705673

Reaktionsgleichung

3-(1-adamantyl)-6-bromo-2-naphthol

sodium hydride

methoxyethoxymethyl chloride

→

7-(1-adamantyl)-6-methoxyethoxymethoxy-2-bromonaphthalene

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe reaction mixture was stirred at room temperature for 2 hours
2. 2
   workup.ADDITIONThe reaction mixture was poured into ice-cold water
3. 3
   Extraktionextracted with ethyl ether
4. 4
   Sonstigethe organic phase was separated
5. 5
   Trocknendried over magnesium sulfate
6. 6
   Sonstigeevaporated
7. 7
   SonstigeThe residue obtained
8. 8
   Sonstigewas purified by chromatography on a silica column
9. 9
   Wascheneluted with a mixture of dichloromethane and heptane (40/60)
10. 10
    Sonstige19.5 g (87%) of the expected compound were collected

Vorschrift

17.85 g (0.05 mol) of 3-(1-adamantyl)-6-bromo-2-naphthol and 200 ml of DMF were introduced into a three-necked flask under a stream of nitrogen. 1.8 g (0.06 mol) of sodium hydride (80% in oil) was added portionwise and the reaction mixture was stirred until gas evolution had ceased. 6.9 ml (0.06 mol) of methoxyethoxymethyl chloride were then added and the reaction mixture was stirred at room temperature for 2 hours. The reaction mixture was poured into ice-cold water and extracted with ethyl ether and the organic phase was separated by settling, dried over magnesium sulfate and evaporated. The residue obtained was purified by chromatography on a silica column eluted with a mixture of dichloromethane and heptane (40/60). 19.5 g (87%) of the expected compound were collected, which compound had a melting point of 99°-100° C.

Quelle