Réaction #2320130

Équation de réaction

2-methylene-3,4-dihydronaphthalen-1-one

ethyl propenyl ether

→

product

2-ethoxy-3-methyl-3,4,5,6-tetrahydrobenzo[h]chromene

Solvants

dichloroethane

Conditions de réaction

Traitement

1. 1
   Températureat reflux under nitrogen
2. 2
   AutreEvaporation of the solvent
3. 3
   workup.WAITleft 200 g of a brown liquid that
4. 4
   Autrewas purified on a silica gel column with 15/85 ethylacetate/hexane as the eluent

Mode opératoire

A solution of 2-methylene-3,4-dihydronaphthalen-1-one (44.9 g, 282 mmol), tris(6,6,7,7,8,8,8-heptafluoro-2,2-dimethyl-3,5-octanedionato)ytterbium [Yb(fod)3, 15.0 g, 14.2 mmo], and ethyl propenyl ether (300 g, 390 mL, 3.5 mol) in 830 mL of dichloroethane was heated at reflux under nitrogen with stirring for 20 hours. Evaporation of the solvent left 200 g of a brown liquid that was purified on a silica gel column with 15/85 ethylacetate/hexane as the eluent, yielding 140 g of product, which was used without further purification.

Source