تفاعل #1714

معادلة التفاعل

Methyl-3-hydroxy-2-naphthoate

sodium hydride

propargyl bromide

→

title compound

المردود 35.0%

Methyl-3-propargyloxy-2-naphthoate

المردود 35.0%

المذيبات

THF

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةthe mixture heated to reflux
2. 2
   workup.WAITAfter 20 h
3. 3
   درجة الحرارةto cool
4. 4
   أخرىevaporated under reduced pressure
5. 5
   أخرىThe residue was then evaporated under reduced pressure
6. 6
   أخرىThe residue was then partitioned between EtOAc and water
7. 7
   استخلاصThe aqueous layer was then extracted with EtOAc (1×)
8. 8
   تجفيفthe combined organic layers were dried (Na2SO4)
9. 9
   أخرىevaporated
10. 10
    أخرىCrystallisation of the oil from petrol (60/80) diethyl ether

الإجراء التجريبي

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%).

المصدر