Diethyl Ether → Methyl (3E)-4-phenyl-3-butenoate

HRID 571443Notes

Reaction equation

HRID 571443 reaction equation
[C:1]1([CH:7]=[CH:8][CH2:9][C:10]([OH:12])=[O:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:13]([O-])([O-])=O.[Cs+].[Cs+].CI.CCOCC>CC(C)=O.[Cl-].[Na+].O>[C:1]1(/[CH:7]=[CH:8]/[CH2:9][C:10]([O:12][CH3:13])=[O:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 929234-Phenyl-3-Butenoic Acid

Product 1

HCID 5370649Methyl (3E)-4-phenyl-3-butenoate

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

4-Phenylbut-3-enoic acid was dissolved in acetone and added to Cs2CO3, then MeI was added. The suspension was refluxed overnight. Et2O and brine were added and the phases separated. Aqueous layer was washed three times with Et2O. Combined organic layers were dried over MgSO4 and the solvent was evaporated in vacuum. (E)-methyl 4-phenylbut-3-enoate (S32) was obtained as a yellow oil (quantitative). Rf (hexane/EtOAc 8:1)=0.28.

Workup

  1. temperatureThe suspension was refluxed overnight
  2. customthe phases separated
  3. washAqueous layer was washed three times with Et2O
  4. dry with materialCombined organic layers were dried over MgSO4
  5. customthe solvent was evaporated in vacuum

Sources & evidence

ORD record
ord-3f03656343a843829469627e6b27d4c6
Source dataset
uspto-grants-2015_05
Patent number
US09024093B2

Reaction notes

Loading…