Ethyl vinyl ether → 1,1-Diphenyl-2-(1-ethenoxy)-hex-5-ene

HRID 909712Notes

Reaction equation

HRID 909712 reaction equation
[CH:1]([CH:14]1[CH2:19][C:18](=O)[CH:17]=[CH:16]O1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:21]([O-:24])(O)=O.[Na+].[CH:26](OCC)=C>[Hg](OC(C(F)(F)F)=O)OC(C(F)(F)F)=O>[C:2]1([CH:1]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:14]([O:24][CH:21]=[CH2:26])[CH2:19][CH2:18][CH:17]=[CH2:16])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8023Ethyl vinyl etherHCID 516892Sodium BicarbonateHCID 666308482-Benzhydryl-2H-pyran-4(3H)-one

Product 1

HCID 666312581,1-Diphenyl-2-(1-ethenoxy)-hex-5-eneYield 66%

Reagents, catalysts & solvents 1

HCID 16685285Hg(TFA)2Catalyst

Procedure

Into a mixture of 1,1-diphenyl-hex-5-en-2-ol 2 (7 g, 27.78 mmol) in ethyl vinyl ether (250 ml) was added Hg(OCOCF3)2 (2.37 g, 5.56 mmol) and was stirred overnight at room temperature. The reaction mixture was neutralized by addition of sat. aqueous NaHCO3. The organic phase was separated and the aqueous layer was extracted with ethyl ether, and dried over anhydrous Na2SO4. Removal of the solvent and purification by flash chromatography (Hexane/Ethyl Acetate 20:1) gave 1,1-diphenyl-2-(1-ethenoxy)-hex-5-ene 9 (5.1 g, 66%) as a liquid.

Workup

  1. customThe organic phase was separated
  2. extractionthe aqueous layer was extracted with ethyl ether
  3. dry with materialdried over anhydrous Na2SO4
  4. customRemoval of the solvent and purification by flash chromatography (Hexane/Ethyl Acetate 20:1)

Sources & evidence

ORD record
ord-a3c000d7e20b4c32aac048efa20c7954
Source dataset
uspto-grants-2011_09
Patent number
US08017791B2

Reaction notes

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