反应详情

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##

1. temperatureheated
2. temperatureto reflux for 18 hrs
3. temperatureThe resulting purple solution was cooled
4. customevaporated
5. customto remove the excess triethylorthoformate
6. customthe residue flash chromatographed over silica (40% diethyl ether in hexane)
7. customto yield an orange gum (0.28 g; yield 34%)