Ethyl 1-propenyl ether → 2-Ethoxy-3-methyl-3,4,5,6-tetrahydrobenzo[h]chromene

HRID 2096092Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2096092
[CH2:1]=[C:2]1[CH2:11][CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]1=[O:12].[CH:13]([O:16][CH2:17][CH3:18])=[CH:14][CH3:15]>ClC(Cl)C.CC(C)(C)/C(/O)=C/C(C(C(C(F)(F)F)(F)F)(F)F)=O.CC(C)(C)/C(/O)=C/C(C(C(C(F)(F)F)(F)F)(F)F)=O.CC(C)(C)/C(/O)=C/C(C(C(C(F)(F)F)(F)F)(F)F)=O.[Yb]>[CH2:17]([O:16][CH:13]1[CH:14]([CH3:15])[CH2:1][C:2]2[CH2:11][CH2:10][C:9]3[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=3[C:3]=2[O:12]1)[CH3:18]

Komponenten

5

Edukt 2

HCID 13570Ethyl 1-propenyl etherHCID 3777512-Methylenetetralin-1-one

Produkt 1

HCID 592948342-Ethoxy-3-methyl-3,4,5,6-tetrahydrobenzo[h]chromeneAusbeute 203,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 5881176(Z)-1,1,1,2,2,3,3-Heptafluoro-6-hydroxy-7,7-dimethyloct-5-en-4-one;ytterbiumKatalysatorHCID 63651,1-DichloroethaneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  1. temperatureat reflux under nitrogen
  2. customEvaporation of the solvent
  3. waitleft 200 g of a brown liquid that
  4. customwas purified on a silica gel column with 15/85 ethylacetate/hexane as the eluent

Quellen und Nachweise

ORD-Eintrag
ord-d5bde7b573ce4de2881d3cba60c508f6
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08449990B2

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