Reacción #527802

Ecuación de reacción

1,1-dianisylprop-2-yn-1-ol

toluene

4-methoxy-2-naphthol

→

3,3-dianisyl-6-methoxy-3H-naphtho[2,1-b]pyran

Disolventes

hexane

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturacooled
2. 2
   Filtraciónfiltered
3. 3
   LavadoThe filtrate was washed with 2M NaOH
4. 4
   Secadowater, dried
5. 5
   Otroevaporated
6. 6
   Otroto give an orange gum

Procedimiento

A mixture of 4-methoxy-2-naphthol (0.26 g; 0.015 mol). 1,1-dianisylprop-2-yn-1-ol (0.40 g g;0.0015 mol), acidic alumina Brockmann 1 (3.5 g) and toluene (40.0 ml) was heated and stirred for 1.5 h, cooled, filtered. The filtrate was washed with 2M NaOH then water, dried and evaporated to give an orange gum. Trituration with hexane yielded 3,3-dianisyl-6-methoxy-3H-naphtho[2,1-b]pyran of formula (1) below as an off-white solid (41%). Crystallisation from hexane and ethylacetate gave the pyran as white micro-platelets, m.pt. 158°-160° C. ##STR8##

Fuente