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

HRID 78894

Reaction equation

HRID 78894 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-0655dd2aa8604b9baf75b92edcc0c846
Source dataset
uspto-grants-2014_09
Patent number
US08841464B2

Linked notes

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