HuagongsheHuagongshe Chemistry Print Report · For research reference only
Ethyl 1-propenyl ether → 2-Ethoxy-3-methyl-3,4,5,6-tetrahydrobenzo[h]chromene
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Ethyl 1-propenyl ether | HCID 13570 | — |
| Reactant | 2-Methylenetetralin-1-one | HCID 377751 | — |
| Catalyst | (Z)-1,1,1,2,2,3,3-Heptafluoro-6-hydroxy-7,7-dimethyloct-5-en-4-one;ytterbium | HCID 5881176 | — |
| Solvent | 1,1-Dichloroethane | HCID 6365 | — |
| Product | 2-Ethoxy-3-methyl-3,4,5,6-tetrahydrobenzo[h]chromene | HCID 59294834 | 203.2% |
Reaction Steps
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.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08449990B2 |
| Source dataset | uspto-grants-2013_05 |
| ORD ID | ord-d5bde7b573ce4de2881d3cba60c508f6 |
| Source note | uspto-grants-2013_05 |