Reacción #1824324

Ecuación de reacción

2-hydroxynaphthalene-1,4-dione

triphenylphosphine

diethyl azodicarboxylate

3-methylbut-2-enol

→

2-(3-methylbut-2-enyloxy)naphthalene-1,4-dione

Rendimiento 59.7%

Disolventes

tetrahydrofuran

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGstirring
2. 2
   workup.WAITwas continued for 2 hours
3. 3
   OtroThe precipitate was collected
4. 4
   Otroair-dried
5. 5
   Otrorecrystallised from aqueous methanol

Procedimiento

To a stirred solution of 2-hydroxynaphthalene-1,4-dione (10.0 g, 57.4 mmol) and triphenylphosphine (15.1 g, 57.4 mmol) in dry tetrahydrofuran (150 ml) at 0° C. under an atmosphere of nitrogen was added diethyl azodicarboxylate (10.0 g, 57.4 mmol). After stirring for a further 5 minutes, a solution of 3-methylbut-2-enol (7.42 g, 86.1 mmol) in dry tetrahydrofuran (10 ml) was added dropwise and stirring was continued for 2 hours. The precipitate was collected, air-dried and recrystallised from aqueous methanol to yield 2-(3-methylbut-2-enyloxy)naphthalene-1,4-dione (8.3 g) as a yellow crystalline solid, m.pt.: 138° C.

Fuente