Реакция #1714

Уравнение реакции

Methyl-3-hydroxy-2-naphthoate

sodium hydride

propargyl bromide

→

title compound

Выход 35.0%

Methyl-3-propargyloxy-2-naphthoate

Выход 35.0%

Растворители

THF

Условия реакции

Обработка

1. 1
   Температураthe mixture heated to reflux
2. 2
   workup.WAITAfter 20 h
3. 3
   Температураto cool
4. 4
   Другоеevaporated under reduced pressure
5. 5
   ДругоеThe residue was then evaporated under reduced pressure
6. 6
   ДругоеThe residue was then partitioned between EtOAc and water
7. 7
   ЭкстракцияThe aqueous layer was then extracted with EtOAc (1×)
8. 8
   Сушкаthe combined organic layers were dried (Na2SO4)
9. 9
   Другоеevaporated
10. 10
    ДругоеCrystallisation of the oil from petrol (60/80) diethyl ether

Методика

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%).

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