반응 #1714

반응 방정식

Methyl-3-hydroxy-2-naphthoate

sodium hydride

propargyl bromide

→

title compound

수율 35.0%

Methyl-3-propargyloxy-2-naphthoate

수율 35.0%

용매

THF

반응 조건

후처리

1. 1
   온도the mixture heated to reflux
2. 2
   workup.WAITAfter 20 h
3. 3
   온도to cool
4. 4
   기타evaporated under reduced pressure
5. 5
   기타The residue was then evaporated under reduced pressure
6. 6
   기타The residue was then partitioned between EtOAc and water
7. 7
   추출The aqueous layer was then extracted with EtOAc (1×)
8. 8
   건조the combined organic layers were dried (Na2SO4)
9. 9
   기타evaporated
10. 10
    기타Crystallisation of the oil from petrol (60/80) diethyl ether

실험 절차

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%).

출처