Reaktion #1714

Reaktionsgleichung

Methyl-3-hydroxy-2-naphthoate

sodium hydride

propargyl bromide

→

title compound

Ausbeute 35.0%

Methyl-3-propargyloxy-2-naphthoate

Ausbeute 35.0%

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe mixture heated to reflux
2. 2
   workup.WAITAfter 20 h
3. 3
   Temperaturto cool
4. 4
   Sonstigeevaporated under reduced pressure
5. 5
   SonstigeThe residue was then evaporated under reduced pressure
6. 6
   SonstigeThe residue was then partitioned between EtOAc and water
7. 7
   ExtraktionThe aqueous layer was then extracted with EtOAc (1×)
8. 8
   Trocknenthe combined organic layers were dried (Na2SO4)
9. 9
   Sonstigeevaporated
10. 10
    SonstigeCrystallisation of the oil from petrol (60/80) diethyl ether

Vorschrift

Methyl-3-hydroxy-2-naphthoate (2.63 g, 0.013 mol) was dissolved in dry THF (80 ml) and treated with sodium hydride (80%) ((0.398 g, 0.013 mol), with stirring under N2. After 0.5 h, propargyl bromide (80% in toluene) (2.57 ml 0.017 mol) was added and the mixture heated to reflux. After 20 h, the reaction mixture was allowed to cool and then evaporated under reduced pressure. The residue was then evaporated under reduced pressure. The residue was then partitioned between EtOAc and water. The aqueous layer was then extracted with EtOAc (1×), and the combined organic layers were dried (Na2SO4) and evaporated to given an orange oil. Crystallisation of the oil from petrol (60/80) diethyl ether provided the title compound as a pale yellow solid (1.0 gg, 35%).

Quelle