반응 #82880

반응 방정식

4-morpholino-2-naphthol

1,3,3-trimethyl-2-methyleneindole

triethylorthoformate

→

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

수율 34.0%

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

수율 34.0%

용매

diethyl ether

반응 조건

후처리

1. 1
   온도heated
2. 2
   온도to reflux for 18 hrs
3. 3
   온도The resulting purple solution was cooled
4. 4
   기타evaporated
5. 5
   기타to remove the excess triethylorthoformate
6. 6
   기타the residue flash chromatographed over silica (40% diethyl ether in hexane)
7. 7
   기타to yield an orange gum (0.28 g; yield 34%)

실험 절차

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##

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