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

HRID 2262366Notes

Reaction equation

HRID 2262366 reaction equation
[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]

Participants

5

Reactant 2

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

Product 1

HCID 592948342-Ethoxy-3-methyl-3,4,5,6-tetrahydrobenzo[h]chromeneYield 203.2%

Reagents, catalysts & solvents 2

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

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-1e73cbe7b45943638b360b110e5f8b9c
Source dataset
uspto-grants-2010_12
Patent number
US07851072B2

Reaction notes

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