Acetic Acid → tert-Butyl 2-[4-(4-oxothian-3-ylidenemethyl)phenyl]propionate

HRID 1685799Notes

Reaction equation

HRID 1685799 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]([CH3:17])[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])=[CH:5][CH:4]=1)=O.[O:18]=[C:19]1[CH2:24][CH2:23][S:22][CH2:21][CH2:20]1.N1CCCCC1.C(O)(=O)C>C1(C)C=CC=CC=1>[O:18]=[C:19]1[CH2:24][CH2:23][S:22][CH2:21][C:20]1=[CH:1][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([CH3:17])[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8082PiperidineHCID 66173Tetrahydrothiopyran-4-oneHCID 86639388Tert-butyl 2-(4-formylphenyl)propionate

Product 1

HCID 86639387tert-Butyl 2-[4-(4-oxothian-3-ylidenemethyl)phenyl]propionateYield 20.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of tert-butyl 2-(4-formylphenyl)propionate (2.0 g), 4-oxothiane (1.2 g) and piperidine (1.0 ml) in toluene (10.0 ml) was added acetic acid (2.0 ml) at room temperature, and then the mixture was refluxed by heating for 3 hours. The reaction mixture was quenched with water, and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and then dried over sodium sulfate. The solvent was evaporated under reduced pressure, and then the residue was purified by silica gel column chromatography (hexane/ethyl acetate=6/1) to give the title compound (570 mg, 20%).

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureby heating for 3 hours
  3. customThe reaction mixture was quenched with water
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with water and saturated brine
  6. dry with materialdried over sodium sulfate
  7. customThe solvent was evaporated under reduced pressure
  8. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=6/1)

Sources & evidence

ORD record
ord-bac48615bb7f4c27b3b65131b2771f77
Source dataset
uspto-grants-2012_04
Patent number
US08148421B2

Reaction notes

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