Réaction #1714

Équation de réaction

Methyl-3-hydroxy-2-naphthoate

sodium hydride

propargyl bromide

→

title compound

Rendement 35.0%

Methyl-3-propargyloxy-2-naphthoate

Rendement 35.0%

Solvants

THF

Conditions de réaction

Traitement

1. 1
   Températurethe mixture heated to reflux
2. 2
   workup.WAITAfter 20 h
3. 3
   Températureto cool
4. 4
   Autreevaporated under reduced pressure
5. 5
   AutreThe residue was then evaporated under reduced pressure
6. 6
   AutreThe residue was then partitioned between EtOAc and water
7. 7
   ExtractionThe aqueous layer was then extracted with EtOAc (1×)
8. 8
   Séchagethe combined organic layers were dried (Na2SO4)
9. 9
   Autreevaporated
10. 10
    AutreCrystallisation of the oil from petrol (60/80) diethyl ether

Mode opératoire

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%).

Source