反応 #1714

反応方程式

Methyl-3-hydroxy-2-naphthoate

sodium hydride

propargyl bromide

→

title compound

収率 35.0%

Methyl-3-propargyloxy-2-naphthoate

収率 35.0%

溶媒

THF

反応条件

後処理

1. 1
   温度the mixture heated to reflux
2. 2
   workup.WAITAfter 20 h
3. 3
   温度to cool
4. 4
   その他evaporated under reduced pressure
5. 5
   その他The residue was then evaporated under reduced pressure
6. 6
   その他The residue was then partitioned between EtOAc and water
7. 7
   抽出The aqueous layer was then extracted with EtOAc (1×)
8. 8
   乾燥the combined organic layers were dried (Na2SO4)
9. 9
   その他evaporated
10. 10
    その他Crystallisation of the oil from petrol (60/80) diethyl ether

実験手順

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%).

出典