Reacción #1714

Ecuación de reacción

Methyl-3-hydroxy-2-naphthoate

sodium hydride

propargyl bromide

→

title compound

Rendimiento 35.0%

Methyl-3-propargyloxy-2-naphthoate

Rendimiento 35.0%

Disolventes

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturathe mixture heated to reflux
2. 2
   workup.WAITAfter 20 h
3. 3
   Temperaturato cool
4. 4
   Otroevaporated under reduced pressure
5. 5
   OtroThe residue was then evaporated under reduced pressure
6. 6
   OtroThe residue was then partitioned between EtOAc and water
7. 7
   ExtracciónThe aqueous layer was then extracted with EtOAc (1×)
8. 8
   Secadothe combined organic layers were dried (Na2SO4)
9. 9
   Otroevaporated
10. 10
    OtroCrystallisation of the oil from petrol (60/80) diethyl ether

Procedimiento

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%).

Fuente