Reacción #82880

Ecuación de reacción

4-morpholino-2-naphthol

1,3,3-trimethyl-2-methyleneindole

triethylorthoformate

→

indoline-2,3'-[3H]-naphtho[2,1-b]pyran

Rendimiento 34.0%

1,3,3-Trimethyl-6'-morpholinospiro[indoline-2,3'-[3H]-naphtho[2,1-b]pyran]

Rendimiento 34.0%

Disolventes

diethyl ether

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturaheated
2. 2
   Temperaturato reflux for 18 hrs
3. 3
   TemperaturaThe resulting purple solution was cooled
4. 4
   Otroevaporated
5. 5
   Otroto remove the excess triethylorthoformate
6. 6
   Otrothe residue flash chromatographed over silica (40% diethyl ether in hexane)
7. 7
   Otroto yield an orange gum (0.28 g; yield 34%)

Procedimiento

A mixture of 4-morpholino-2-naphthol (0.47 g;0.002 mol), prepared as in 2(b) above, 1,3,3-trimethyl-2-methyleneindole (0.8 g;0.0022 mol) and triethylorthoformate (10.0 ml) was stirred under nitrogen and heated to reflux for 18 hrs. The resulting purple solution was cooled and evaporated to remove the excess triethylorthoformate and the residue flash chromatographed over silica (40% diethyl ether in hexane) to yield an orange gum (0.28 g; yield 34%). Trituration of the gum with diethyl ether afforded the 1,3,3-trimethyl-6'-morpholinospiro [indoline-2,3'-[3H]-naphtho[2,1-b]pyran having the structure shown below as a pale brown solid, m.pt 191°-194° C. ##STR20##

Fuente