Réaction #82880

Équation de réaction

4-morpholino-2-naphthol

1,3,3-trimethyl-2-methyleneindole

triethylorthoformate

→

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

Rendement 34.0%

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

Rendement 34.0%

Solvants

diethyl ether

Conditions de réaction

Traitement

1. 1
   Températureheated
2. 2
   Températureto reflux for 18 hrs
3. 3
   TempératureThe resulting purple solution was cooled
4. 4
   Autreevaporated
5. 5
   Autreto remove the excess triethylorthoformate
6. 6
   Autrethe residue flash chromatographed over silica (40% diethyl ether in hexane)
7. 7
   Autreto yield an orange gum (0.28 g; yield 34%)

Mode opératoire

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##

Source